Benzaldehyde → HCID 54048955, compound

HRID 1757159Notes

Reaction equation

HRID 1757159 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C@H:5]([CH2:7][C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:11]([CH2:21][CH2:22][CH2:23][CH3:24])=[N:10][CH:9]=1)[NH2:6])[CH3:2].[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([BH3-])#N.[Na+]>>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:12]1[C:8]([CH2:7][C@@H:5]([C:4]([OH:3])=[O:25])[NH:6][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:9][N:10]=[C:11]1[CH2:21][CH2:22][CH2:23][CH3:24].[CH2:1]([O:3][C:4](=[O:25])[C@H:5]([CH2:7][C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:11]([CH2:21][CH2:22][CH2:23][CH3:24])=[N:10][CH:9]=1)[NH:6][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:2]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 54253690HCID 54253690, compound

Product 2

HCID 54048955HCID 54048955, compoundHCID 54567190HCID 54567190, compound

Procedure

The title compound is prepared by reductive alkylation of 2-n-butyl-3-(2-chlorophenyl)methylhistidine ethyl ester with benzaldehyde in the presence of sodium cyanoborohydride to give 3-[(2-chlorophenyl)methyl]-2-n-butyl-N-benzylhistidine ethyl ester. Hydrolysis of the ester group is accomplished according to Example 2 (iii) to provide the title compound.

Sources & evidence

ORD record
ord-729140e9aee84c428bc1edacef948946
Source dataset
uspto-grants-1995_08
Patent number
US05444081

Reaction notes

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