Sodium Hydroxide → HCID 178448443, compound

HRID 466847Notes

Reaction equation

HRID 466847 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 triturated with 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
  4. customThe crude product was triturated with diethyl ether

Sources & evidence

ORD record
ord-d4ea22e3b5ef4312a56e64ddd2339ef2
Source dataset
uspto-grants-1992_10
Patent number
US05157041

Reaction notes

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