Potassium Carbonate → (R)-(-)-1-tert-butylcarbonylmethyl-2-oxo-3-phenoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 352381Notes

Reaction equation

HRID 352381 reaction equation
C(O)(=O)C(O)=O.[C:7]([C:11]([CH2:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:17][C@@H:16]([NH2:31])[C:15]1=[O:32])=[O:12])([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+].[C:39](Cl)(=[O:47])[O:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(OCC)(=O)C>[C:7]([C:11]([CH2:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:17][C@@H:16]([NH:31][C:39]([O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:47])[C:15]1=[O:32])=[O:12])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 11190073(R)-(-)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine oxalate

Product 1

HCID 69908453(R)-(-)-1-tert-butylcarbonylmethyl-2-oxo-3-phenoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 96.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 8.9 g of (R)-(−)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine oxalate in 45 ml of ethyl acetate was added 45 ml of an aqueous solution of 8.25 g of potassium carbonate under ice cooling. The mixture was stirred at the same temperature for 30 minutes. After addition of 3.12 g of phenyl chlorocarbonate under ice cooling, the mixture was stirred for 5 minutes under ice cooling and then at room temperature for 30 minutes. The reaction mixture was then separated into layers. The aqueous layer was extracted with ethyl acetate and the organic layer thus obtained was combined with the organic layer obtained in advance. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure, whereby 9.19 g of the title compound was obtained.

Workup

  1. stirringthe mixture was stirred for 5 minutes under ice cooling
  2. waitat room temperature for 30 minutes
  3. customThe reaction mixture was then separated into layers
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. customthe organic layer thus obtained
  6. customobtained in advance
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-abb02411a47542dda22314978357b397
Source dataset
uspto-grants-2004_06
Patent number
US06747022B2

Reaction notes

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