Cesium carbonate → HCID 18652406, compound

HRID 1587483Notes

Reaction equation

HRID 1587483 reaction equation
[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[O:18])[C@H:9]([NH:19][C:20]([O:22][CH:23]([CH3:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-:32].[Cs+].[Cs+].[N:37]1([CH:42](I)[C:43](N)=O)[CH2:41][CH2:40][CH2:39][CH2:38]1>CN(C)C=O>[N:37]1([C:42]([CH2:43][N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][C@@H:9]([NH:19][C:20]([O:22][CH:23]([CH3:30])[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[C:10]2=[O:18])=[O:32])[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 19758307HCID 19758307, compoundHCID 53950618HCID 53950618, compound

Product 1

HCID 18652406HCID 18652406, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1,3-Dihydro-5-phenyl-3(R)-{[(α-methyl)benzyloxycarbonyl]-amino}-2H-1,4-benzodiazepin-2-one (100 mg, 0.25 mmole) in 2 ml of dry N,N-dimethylformamide was stirred magnetically in an ice bath under an inert atmosphere. Cesium carbonate (106 mg, 0.325 mmole) and pyrrolidinyliodoacetamide (78 mg, 0.325 mmole) were added and the reaction mixture was stirred vigorously at 0° C. for 1.75 hours. The reaction mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were washed with brine. The crude product was chromatographed on three, 1 mm×20 cm×20 cm precoated silica gel plates (3:2 hexane-ethyl acetate elution) to give 109 mg of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. customThe crude product was chromatographed on three, 1 mm×20 cm×20 cm precoated silica gel plates (3:2 hexane-ethyl acetate elution)

Sources & evidence

ORD record
ord-6ed1e09a6ade4818b6a0b14169dd4cf6
Source dataset
uspto-grants-1993_06
Patent number
US05218115

Reaction notes

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