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

HRID 2230469Notes

Reaction equation

HRID 2230469 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:25])[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][C@H:7]([NH:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:6]1=[O:35].CO.O.O[Li].O>C1COCC1>[O:35]=[C:6]1[N:5]([CH2:4][C:3]([OH:36])=[O:2])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:25])[CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:8][C@@H:7]1[NH:26][C:27](=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57159598(3S)-2-Oxo-3-benzoylamino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

Product 1

HCID 68498710(3S)-2-Oxo-3-benzoylamino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acidYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3S)-2-Oxo-3-benzoylamino-5-(3-phenylpropionyl-2,3,4,5-tertrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester (602a; 1.25 g, 2.57 mmol) was dissolved in 11 ml of THF, MeOH and H2O (5:5:1) and treated with LiOH.H2O (42 mg, 0.62 mmol) stirred at RT for 64 h. The reaction was concentrated in vacuo, diluted with H2O and acidified with aq. 1N HCl to give 230 mg of 603a as a white solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with H2O

Sources & evidence

ORD record
ord-34eb56919698451883432219c9d0ff6a
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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