* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
3-{(4Z,10Z,15Z,19Z)-18-[2-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyl)-ethyl]-3,8,13,17-tetramethyl-7,12-divinyl-22,24-dihydro-porphin-2-yl}-propionic acid[ No CAS ]
H-GGG-D(OtBu)PAALK(Boc)R(Pbf)AR(Pbf)N(Trt)T(tBu)E(OtBu)AAR(Pbf)R(Pbf)S(tBu)R(Pbf)AR(Pbf)K(Boc)LQ(Trt)R(Pbf)-NH-Novasyn TGR resin[ No CAS ]
protoporphyrin IX(-Cys-NH2)(-GGG-DPAALKRARNTEAARRSRARKLQR-NH2)[ No CAS ]
(2R)-2-([14-(2-butynyloxy)phenyl]sulfonyl}amino)-3-(tritylsulfanyl)propanamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With triethylamine; In dichloromethane; for 13h;
Example 13 (2R)-2-([14-(2-Butynyloxy)phenyl]sulfonyl}amino)-3-(tritylsulfanyl)propanamide To a solution of 1.203g (3.685 mmol) of the primary amide product fromExample 12 and 1.39 ML (10 mmol) of triethylamine in 20 ML of methylene chloride was added in one portion 0.954g (3.9 mmol) of 4-but-2-ynyloxy-benzenesulfonyl chloride.. After stirring for 13h, 50 ML of dichloromethane and 50 ML of water were added.. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated in vacuo and subjected to flash chromatography eluding with hexanes/ethyl acetate (1:1) to furnish 1.65g (79%) of the desired sulfonamide as a white solid.. Electrospray Mass Spec: 1139.6 (2M-H)
To 2.68g (7.37 mmol) of S-trityl-L-cysteine and 40 mL of methanol was added 7 mL (96 mmol) of thionyl chloride dropwise. After heating at reflux for 6h the solution was cooled to room temperature and then concentrated in vacuo. The resulting residue was taken up in 20 mL of methanol, treated with activated carbon, filtered and concentrated in vacuo yielding the methyl ester as an off-white foam. This material was dissolved in 6 mL of methanol in a sealable tube and cooled to -78. After 30 mL of liquid ammonia was added, the tube was sealed and the reaction was stirred at room temperature for 14h After recooling to -78 the reaction tube was unsealed and the solution was carefully reduced to dryness. The residue was chromatographed on silica gel eluting with methylene chloride/methanol (10:1) furnishing 1.52g (57%) of the primary amide as a white solid. Electrospray Mass Spec: 363.2 (M+H)+
(2R)-2-([14-(2-butynyloxy)phenyl]sulfonyl}amino)-3-(tritylsulfanyl)propanamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In dichloromethane; water; 4-but-2-ynyloxybenzenesulfonyl chloride;
EXAMPLE 13 (2R)-2-([4-(2-Butynyloxy)phenyl]sulfonyl}amino)-3-(tritylsulfanyl)propanamide To a solution of 1.203 g (3.685 mmol) of the primary amide product from Example 12 and 1.39 mL (10 mmol) of triethylamine in 20 mL of methylene chloride was added in one portion 0.954 g (3.9 mmol) of 4-but-2-ynyloxy-benzenesulfonyl chloride. After stirring for 13 h, 50 mL of dichloromethane and 50 mL of water were added. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated in vacuo and subjected to flash chromatography eluding with hexanes/ethyl acetate (1:1) to furnish 1.65 g (79%) of the desired sulfonamide as a white solid. Electrospray Mass Spec: 1139.6 (2M-H)-
EXAMPLE 12 (2R)-2-Amino-3-(tritylsulfanyl)propanamide To 2.68 g (7.37 mmol) of S-trityl-L-cysteine and 40 mL of methanol was added 7 mL (96 mmol) of thionyl chloride dropwise. After heating at reflux for 6 h the solution was cooled to room temperature and then concentrated in vacuo. The resulting residue was taken up in 20 mL of methanol, treated with activated carbon, filtered and concentrated in vacuo yielding the methyl ester as an off-white foam. This material was dissolved in 6 mL of methanol in a sealable tube and cooled to -78.
Chemistry
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120K+ Compounds
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