Methanol → Glycine, N-(4-chloro-5-iodo-2-methoxyphenyl)-, methyl ester

HRID 588817Notes

Reaction equation

HRID 588817 reaction equation
C([CH:5]([NH:9][C:10]1[CH:15]=[C:14]([I:16])[C:13]([Cl:17])=[CH:12][C:11]=1[O:18][CH3:19])[C:6]([OH:8])=[O:7])(C)(C)C.O=S(Cl)Cl.[CH3:24]O>>[Cl:17][C:13]1[C:14]([I:16])=[CH:15][C:10]([NH:9][CH2:5][C:6]([O:8][CH3:24])=[O:7])=[C:11]([O:18][CH3:19])[CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 131734448Tert-butyl 2-(4-chloro-5-iodo-2-methoxyphenylamino)acetic acid

Product 1

HCID 117610930Glycine, N-(4-chloro-5-iodo-2-methoxyphenyl)-, methyl ester

Procedure

A mixture of tert-butyl 2-(4-chloro-5-iodo-2-methoxyphenylamino)acetic acid (3.0 g, 8.7 mmol), SOCl2 (3 mL) in MeOH (20 mL) was stirred at reflux for 2 h. The mixture was concentrated in vacuo to yield the crude product (3.1 g) as a yellow solid.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e0059a0200564c369a12efd96f0e2640
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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