Hydrochloric Acid → HCID 178491197, compound

HRID 1252527Notes

Reaction equation

HRID 1252527 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:31][C:32](=[O:51])[NH:33][CH:34]([C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=1)[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[C:13]([NH:15][C@@H:16]([C@H:21]([NH:23][CH2:24][CH2:25][C:26]1[N:27]=[CH:28][NH:29][CH:30]=1)[CH3:22])[C:17]([O:19]C)=[O:18])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO.[OH-].[Na+]>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:31][C:32](=[O:51])[NH:33][CH:34]([C:43]1[CH:44]=[CH:45][C:46]([O:49][CH3:50])=[CH:47][CH:48]=1)[C:35]1[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=1)[C:13]([NH:15][C@@H:16]([C@H:21]([NH:23][CH2:24][CH2:25][C:26]1[N:27]=[CH:28][NH:29][CH:30]=1)[CH3:22])[C:17]([OH:19])=[O:18])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178501511HCID 178501511, compound

Product 1

HCID 178491197HCID 178491197, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl (2S,3R)-2-[[(2S)-2-benzyloxycarbonylamino-3-[N-[bis(4-methoxyphenyl)methyl]carbamoyl]propionyl]amino]-3-[[2-(4-imidazolyl)ethyl]amino]butyrate (1.40 g) in a mixture of methanol (50 ml) and 1N aqueous sodium hydroxide (25 ml) was stirred for 30 minutes at room temperature and the mixture was adjusted to pH 7 with 1N hydrochloric acid. The precipitate was collected by filtration to give (2S,3R)-2-[[(2S)-2-benzyloxycarbonylamino-3-[N-[bis(4-methoxyphenyl)methyl]carbamoyl]propionyl]amino]-3-[[2-(4-imidazolyl)ethyl]amino]butyric acid (1.16 g) as a white powder.

Workup

  1. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-297fa44475834bfa9e58329dece51fb6
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

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