Potassium Carbonate → (3RS)-1-(2-hydroxylethyl)-3-tert-butoxycarbonylamino-5-(2-fluorophenyl)-2, 3-dihydro-1H-1,4-benzodiazepin-2-one

HRID 963461Notes

Reaction equation

HRID 963461 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[N:10][CH:9]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:8]1=[O:33])(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:4][CH2:5][CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[N:10][CH:9]([NH:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[C:8]1=[O:33]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19081175(3RS)-1-(2-acetoxyethyl)-3-tert-butoxycarbonylamino-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Product 1

HCID 54123423(3RS)-1-(2-hydroxylethyl)-3-tert-butoxycarbonylamino-5-(2-fluorophenyl)-2, 3-dihydro-1H-1,4-benzodiazepin-2-oneYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3RS)-1-(2-acetoxyethyl)-3-tert-butoxycarbonylamino-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (0.83 g) in 85 % aqueous ethanol (20 ml) was added potassium carbonate (0.19 g). The mixture was warmed at 65°-70° C. under stirring for 3 hours. Ethanol was removed in vacuo from the reaction mixture and to the aqueous residue was added water (50 ml). The resultant precipitate was collected by filtration, washed with water and dried under reduced pressure to afford (3RS)-1-(2-hydroxylethyl)-3-tert-butoxycarbonylamino-5-(2-fluorophenyl)-2, 3-dihydro-1H-1,4-benzodiazepin-2-one (0.75 g) as a white crystalline powder, which was used in a following reaction step without further purification.

Workup

  1. temperatureThe mixture was warmed at 65°-70° C.
  2. customEthanol was removed in vacuo from the reaction mixture and to the aqueous residue
  3. additionwas added water (50 ml)
  4. filtrationThe resultant precipitate was collected by filtration
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-e92943f5d4794d95af2b2dfae55fe103
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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