Hydrochloric Acid → (S)-3-(3,4-Bis(benzyloxy)phenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoic acid

HRID 58901Notes

Reaction equation

HRID 58901 reaction equation
[Li+].[OH-].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH2:25][C@H:26]([NH:37][C:38](=[O:51])[C@@H:39]([NH:41][C:42](=[O:50])[CH2:43][N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)[CH3:40])[C:27]([O:29]CC2C=CC=CC=2)=[O:28])[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>O.CO>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH2:25][C@H:26]([NH:37][C:38](=[O:51])[C@@H:39]([NH:41][C:42](=[O:50])[CH2:43][N:44]2[CH2:45][CH2:46][O:47][CH2:48][CH2:49]2)[CH3:40])[C:27]([OH:29])=[O:28])[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 130394541(S)-benzyl 3-(3,4-bis(benzyloxy)phenyl)-2-((S)-2-(2-morpholinoacetamido) propanamido)propanoate

Product 1

HCID 117690516(S)-3-(3,4-Bis(benzyloxy)phenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of LiOH (279 mg, 6.6 mmol) in water (6 mL) was added to a solution of (S)-benzyl 3-(3,4-bis(benzyloxy)phenyl)-2-((S)-2-(2-morpholinoacetamido) propanamido)propanoate (1.1 g, 1.66 mmol) in MeOH (30 mL) at 0° C. with stirring. The reaction mixture was stirred for 3 h and then acidified with 2 N aqueous HCl to pH=3. The resulting mixture was concentrated and the residue was carried forward without further purification.

Workup

  1. stirringThe reaction mixture was stirred for 3 h
  2. concentrationThe resulting mixture was concentrated
  3. customthe residue was carried forward without further purification

Sources & evidence

ORD record
ord-a7b40964151544c9abd43c9c91575870
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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