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

HRID 1493451Notes

Reaction equation

HRID 1493451 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-b1c90f16bdba472a9a459e0e07e1f52f
Source dataset
uspto-grants-1991_06
Patent number
US05021430

Reaction notes

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