(3S)2-Oxo-3-benzoylamino-5-acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid → (3S)-2-Oxo-3-benzoylamino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

HRID 613717Notes

Reaction equation

HRID 613717 reaction equation
O=C1N(CC(O)=O)C2C=CC=CC=2N(C(=O)C)C[C@@H]1N[C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:29]([O:36][C:37](=[O:63])[CH2:38][N:39]1[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[N:43]([C:50](=[O:52])[CH3:51])[CH2:42][C@H:41]([NH:53][C:54](=[O:61])[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:40]1=[O:62])C1C=CC=CC=1>CO.[Pd]>[CH3:29][O:36][C:37](=[O:63])[CH2:38][N:39]1[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[N:43]([C:50](=[O:52])[CH2:51][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:42][C@H:41]([NH:53][C:54](=[O:61])[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:40]1=[O:62]

Participants

5

Reactant 2

HCID 18396555(3S)2-Oxo-3-benzoylamino-5-acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acidHCID 57124097(3S)-2-oxo-3-(benzoylamino)-5-acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid benzyl ester

Product 1

HCID 57159598(3S)-2-Oxo-3-benzoylamino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Method B. (3S)2-Oxo-3-benzoylamino-5-acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid (603d). A mixture of (3S)-2-oxo-3-(benzoylamino)-5-acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid benzyl ester (602d; 510 mg, 1.08 mmol) and 5% Pd/C (250 mg) in MeOH (10 ml) stirred under H2 (1 atm) for 0.5 h. The reaction was filtered and concentrated in vacuo 410 mg of 603d as a white solid.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo 410 mg of 603d as a white solid

Sources & evidence

ORD record
ord-393528d6890540caa54c3ef93bf88ac7
Source dataset
uspto-grants-1999_12
Patent number
US06008217

Reaction notes

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