Benzaldehyde → HCID 53992031, compound

HRID 2230468Notes

Reaction equation

HRID 2230468 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:29])[CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:26])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9][CH:8]([NH2:27])[C:7]1=[O:28].[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])(=O)C.[Na+].[BH3-]C#N.[Na+].Cl>CO.CCOC(C)=O.C(Cl)Cl>[CH3:2][O:3][C:4](=[O:29])[CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:26])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9][CH:8]([NH:27][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:7]1=[O:28]

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 77227190HCID 77227190, compound

Product 1

HCID 53992031HCID 53992031, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A solution of (3S) 2-oxo-3-amino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester hydrochloride (560 mg, 1.34 mmol), benzaldehyde (146 mg, 1.34 mmol) and sodium acetate (220 mg, 2.68 mmol) in methanol (20 ml) was treated with 4A sieves (2 g) and NaCNBH3 (168 mg, 2.68 mmol). The reaction was stirred for 2.5 h, acidified with 10 aq. HCl to pH 2 and washed with Et2O (2×75 ml). The organic layers were concentrated in vacuo to give an oil. Chromatography (flash, SiO2, 0 to 35% EtOAc/CH2Cl2) gave 250 mg (40%) of 602v as a clear oil.

Workup

  1. washwashed with Et2O (2×75 ml)
  2. concentrationThe organic layers were concentrated in vacuo
  3. customto give an oil

Sources & evidence

ORD record
ord-98d71f2c8126450dba178f1620ab6ca4
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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