Imidazole → HCID 57771550, compound

HRID 2070594Notes

Reaction equation

HRID 2070594 reaction equation
[OH:1][C@@H:2]([CH2:10][O:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:3][CH2:4][O:5][S:6]([CH3:9])(=[O:8])=[O:7].N1C=CN=C1.[C:21]([Si:25](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])([CH3:23])[CH3:22].O>CN(C)C=O>[Si:25]([O:1][C@@H:2]([CH2:10][O:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:3][CH2:4][O:5][S:6]([CH3:9])(=[O:8])=[O:7])([C:21]([CH3:24])([CH3:23])[CH3:22])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 57771617HCID 57771617, compound

Product 1

HCID 57771550HCID 57771550, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methanesulfonic acid (R)-3-hydroxy-4-methanesulfonyloxy-butyl ester (7.5 g) obtained in Step 1 in N,N-dimethylformamide (30 mL) were added imidazole (2.9 g) and tert-butylchlorodiphenylsilane (10.3 mL) under ice-cooling, followed by stirring the reaction mixture at room temperature for 12 hours. To the reaction mixture was added water under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:2 to 1:1) to give methanesulfonic acid (R)-3-(tert-butyldiphenylsilanyloxy)-4-methanesulfonyloxy-butyl ester (11.4 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:2 to 1:1)

Sources & evidence

ORD record
ord-b9624fdf755b409c81d0fcac01aaf463
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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