Sodium Hydroxide → tert-butyl(2S,3S)-1-acetyl-8-cyano-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

HRID 1486088Notes

Reaction equation

HRID 1486088 reaction equation
C([N:4]1[C:10](=[O:11])[C@@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:8]([CH3:20])[N:7]([C:21](=[O:23])[CH3:22])[C:6]2[CH:24]=[C:25]([C:28]#[N:29])[CH:26]=[CH:27][C:5]1=2)(=O)C.[OH-].[Na+]>CO.CCOC(C)=O>[C:21]([N:7]1[C@@H:8]([CH3:20])[C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:18])[CH3:16])[C:10](=[O:11])[NH:4][C:5]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:6]1=2)(=[O:23])[CH3:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 131736780tert-butyl(3S,4S)-1,5-diacetyl-7-cyano-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

Product 1

HCID 131736779tert-butyl(2S,3S)-1-acetyl-8-cyano-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamateYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a rt solution of tert-butyl(3S,4S)-1,5-diacetyl-7-cyano-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (413 mg, 1.03 mmol) in MeOH (10.3 ml) was added 1 M aq. sodium hydroxide (1.13 ml, 1.13 mmol), dropwise. The reaction was stirred for 30 min, then diluted with EtOAc, washed with H2O and sat. aq. NaCl, dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash chromatography to provide tert-butyl(2S,3S)-1-acetyl-8-cyano-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (144 mg, 39%) as a white solid. MS m/z 381 (MNa)+.

Workup

  1. washwashed with H2O and sat. aq. NaCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-7d7d21a7c4b04f91b215f15e4cedecd9
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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