Sodium Hydroxide → HCID 178448443, compound

HRID 1757729Notes

Reaction equation

HRID 1757729 reaction equation
[N:1]#[N:2].[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:31]([NH:33][C@@H:34]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C@H:35]([OH:49])[CH2:36][C@@:37]1([C:46]([NH2:48])=[O:47])[CH2:41][CH2:40][CH2:39][N:38]1[C:42]([CH3:45])([CH3:44])[CH3:43])=[O:32])[CH2:15][C:16]1[N:20](C(OCC2C=CC=CC=2)=O)[CH:19]=[N:18][CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+]>Cl>[N:1]#[N:2].[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:31]([NH:33][C@@H:34]([CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[C@H:35]([OH:49])[CH2:36][C@@:37]1([C:46]([NH2:48])=[O:47])[CH2:41][CH2:40][CH2:39][N:38]1[C:42]([CH3:45])([CH3:44])[CH3:43])=[O:32])[CH2:15][C:16]1[N:20]=[CH:19][NH:18][CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86746234HCID 86746234, compound

Product 1

HCID 178448443HCID 178448443, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 30 mg of N2 -[3(S)-[[N,3-bis(benzyloxycarbonyl)-L-histidyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide in 6 ml of 2M hydrochloric acid was stirred at room temperature overnight. The mixture was neutralized by the addition of 2M sodium hydroxide solution and extracted with two 10 ml portions of dichloromethane. The combined extracts were dried over anhydrous sodium sulphate and evaporated. The crude product was trituratedwith diethyl ether to give 14 mg of N2 -[3(S)-[[N-(benzyloxycarbonyl)-L-histidyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide as a white solid of melting point 100° C. (decomposition); MS: m/e 604 [M]+.

Workup

  1. extractionextracted with two 10 ml portions of dichloromethane
  2. dry with materialThe combined extracts were dried over anhydrous sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-1bcafeea740f4a72abfdf241b0c6d418
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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