tert-Butyldimethylsilyl chloride → (1r)-1-{[2(s)-(Hex-5-enyl-methyl-carbamoyl)-4(r)-tert-butyldimethylsilyloxy-pyrrolidine-n-carbonyl]-amino}-2(r)-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 420048Notes

Reaction equation

HRID 420048 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:9]([O:11][C:12]([C@@:14]1([NH:19][C:20]([N:22]2[CH2:26][C@H:25]([OH:27])[CH2:24][C@H:23]2[C:28](=[O:37])[N:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])[CH3:30])=[O:21])[CH2:16][C@@H:15]1[CH:17]=[CH2:18])=[O:13])[CH3:10]>C(Cl)Cl>[CH2:9]([O:11][C:12]([C@@:14]1([NH:19][C:20]([N:22]2[CH2:26][C@H:25]([O:27][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:24][C@H:23]2[C:28](=[O:37])[N:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])[CH3:30])=[O:21])[CH2:16][C@@H:15]1[CH:17]=[CH2:18])=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 66650543(1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 66650529(1r)-1-{[2(s)-(Hex-5-enyl-methyl-carbamoyl)-4(r)-tert-butyldimethylsilyloxy-pyrrolidine-n-carbonyl]-amino}-2(r)-vinyl-cyclopropanecarboxylic acid ethyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, the tert-butyldimethylsilyl chloride was added to a solution of compound 50 (750 mg, 1 eq.) and TEA (537 μL, 1 eq.) in DCM (6 mL). The reaction mixture was stirred overnight at room temperature and quenched with water. The organic layer was washed with brine, dried on sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to yield compound 51 in 70% yield.

Workup

  1. customquenched with water
  2. washThe organic layer was washed with brine
  3. customdried on sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-416d67c4673f4d199f30a2a61cd8a1e3
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

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