Hydrochloric Acid → HCID 70247690, compound

HRID 1533283Notes

Reaction equation

HRID 1533283 reaction equation
C[O:2][C:3](=[O:46])[C@H:4]([CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)[NH:5][C:6](=[O:35])[CH:7]([C:26]1[CH:31]=[CH:30][C:29]2[O:32][CH2:33][O:34][C:28]=2[CH:27]=1)[CH:8]([OH:25])[C:9]1[N:10]=[C:11]([CH2:21][CH2:22][CH2:23][CH3:24])[N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:13]=1.Cl>[OH-].[Na+].CO.C(OCC)(=O)C>[OH:25][CH:8]([C:9]1[N:10]=[C:11]([CH2:21][CH2:22][CH2:23][CH3:24])[N:12]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH:13]=1)[CH:7]([C:26]1[CH:31]=[CH:30][C:29]2[O:32][CH2:33][O:34][C:28]=2[CH:27]=1)[C:6]([NH:5][C@H:4]([C:3]([OH:46])=[O:2])[CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)=[O:35]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 70248573HCID 70248573, compound

Product 1

HCID 70247690HCID 70247690, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-[(2RS,3SR)-3-hydroxy-2-(3,4-methylenedioxyphenyl)-3-(2-n-butyl-1-tert-butoxycarbonyl-1H-imidazol-4-yl)propionyl]-L-tryptophan methyl ester (118 mg) in 1N aqueous sodium hydroxide solution (1.0 ml) and methanol (5.0 ml) was stirred at ambient temperature for 2 hours. The solution was acidified with 1N hydrochloric acid and the mixture was diluted with ethyl acetate followed by washing with brine. The organic layer was dried and evaporated to afford crude N-[(2RS,3SR)-3-hydroxy-2-(3,4-methylenedioxyphenyl)-3-(2-n-butyl-1-tert-butoxycarbonyl-1H-imidazol-4-yl)propionyl]-L-tryptophan.

Workup

  1. washby washing with brine
  2. customThe organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-4270f4797a8f4a8f8af83dee1c2667aa
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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