TERT-BUTOXYCARBONYLAMINO-(4-METHOXY-PHENYL)-ACETIC ACID synthesis

4synthesis methods

Product Name:TERT-BUTOXYCARBONYLAMINO-(4-METHOXY-PHENYL)-ACETIC ACID
CAS Number:55362-76-0
Molecular formula:C14H19NO5
Molecular Weight:281.3

24424-99-5 Synthesis

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TERT-BUTOXYCARBONYLAMINO-(4-METHOXY-PHENYL)-ACETIC ACID

55362-76-0
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Yield:55362-76-0 77%

Reaction Conditions:

Stage #1: di-tert-butyl dicarbonate;2-(4-methoxyphenyl)glycinewith sodium hydroxide in tetrahydrofuran;water at 20; for 15 h;
Stage #2: with hydrogenchloride in water; pH=1;Cooling;

Steps:

16

To a suspension of 2-amino-2-(4-methoxyphenyl)acetic acid (360 mg, 1.99 mmol) in THF (30 ml) and water (30 ml), 2N sodium hydroxide (20 ml, 40.0 mmol) and di-tert-butyl dicarbonate (867 mg, 3.97 mmol) were added. The reaction was stirred at RT for 15h. THF was evaporated, and the remaining aqueous phase was cooled and acidified with 37% HCl until pH 1. The desired compound was extracted with EtOAc and the organic phase was washed with brine, dried over Na₂SO₄ and evaporated to afford 2-(tert- butoxycarbonylamino)-2-(4-methoxyphenyl)acetic acid (430 mg; 77% yield).

References:

WO2012/69275,2012,A1 Location in patent:Page/Page column 58-59