Imidazole → HCID 14430629, compound

HRID 1976232Notes

Reaction equation

HRID 1976232 reaction equation
[OH:1][C@H:2]1[CH2:11][N:10]2[C@H:4]([C:5](=[O:17])[NH:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9]2=[O:12])[CH2:3]1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C)C=O>[Si:23]([O:1][C@H:2]1[CH2:11][N:10]2[C@H:4]([C:5](=[O:17])[NH:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9]2=[O:12])[CH2:3]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2755917HCID 2755917, compound

Product 1

HCID 14430629HCID 14430629, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (2R,11aS)-2-hydroxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo(2,1-c][1,4]benzodiazepin-5,11-dione (50 g) prepared in Reference Example 21 and imidazole (33.7 g) in N,N-dimethylformamide (500 ml), there was added 37.9 g of tert-butyldimethylsilyl chloride at room temperature in a nitrogen gas atmosphere and the mixture was stirred at room temperature for 3 hours. The reaction solution was poured into one liter of ice water and the crystals precipitated were recovered by filtration. The crystals were washed with water and then dried to give 72.5 g (yield 99.9%) of (2R,11aS)-2-(tert-butyldimethylsilyloxy)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione as white crystals.

Workup

  1. customthe crystals precipitated
  2. filtrationwere recovered by filtration
  3. washThe crystals were washed with water
  4. customdried

Sources & evidence

ORD record
ord-1314450e47854b9fa996bb20541617a9
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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