Hydrochloric Acid → N-[4-(2-pyridylaminocarbonyl)-(S,S)-2,4-dibenzylbutyryl]S-benzyl-(L)-cysteine

HRID 374325Notes

Reaction equation

HRID 374325 reaction equation
C[O:2][C:3](=[O:43])[C@H:4]([CH2:34][S:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH:5][C:6](=[O:33])[C@H:7]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:8][C@H:9]([C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+].Cl>CO>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:19][C:17]([C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:8][C@@H:7]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:6]([NH:5][C@H:4]([C:3]([OH:43])=[O:2])[CH2:34][S:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:33])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18645479N-[4-(2-pyridylamino-carbonyl)-(S,S)-2,4-dibenzylbutyryl]-S-benzyl-(L)-cysteine methyl ester

Product 1

HCID 14997157N-[4-(2-pyridylaminocarbonyl)-(S,S)-2,4-dibenzylbutyryl]S-benzyl-(L)-cysteine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.3 g of N-[4-(2-pyridylaminocarbonyl)-(S,S)-2,4-dibenzylbutyryl]-S-benzyl-(L)-cysteine methyl ester and 1 ml of 1N sodium hydroxide in 2 ml of methanol is stirred at room temperature overnight. To the solution is added 1.1 ml of 1N hydrochloric acid. The solution is concentrated, diluted with water, the solid is collected and dried under high vacuum to give N-[4-(2-pyridylaminocarbonyl)-(S,S)-2,4-dibenzylbutyryl]-S-benzyl-(L)-cysteine, melting at 75°-80°; [alpha]D =+22.9°.

Workup

  1. concentrationThe solution is concentrated
  2. additiondiluted with water
  3. customthe solid is collected
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-7abb3ba0a48b4b5a9c3c72655e8aafa9
Source dataset
uspto-grants-1992_11
Patent number
US05166212

Reaction notes

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