Allyl chloroformate → HCID 131733462, compound

HRID 2278371Notes

Reaction equation

HRID 2278371 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([C:7]1[S:8][C:9]([C@@H:12]([NH2:17])[C:13]([F:16])([F:15])[F:14])=[CH:10][CH:11]=1)[CH2:5][OH:6].CCN(C(C)C)C(C)C.Cl[C:28]([O:30][CH2:31][CH:32]=[CH2:33])=[O:29].[Si:34](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35].CN(C1C=CC=CN=1)C>ClCCl>[CH2:31]([O:30][C:28](=[O:29])[NH:3][C@@H:4]([C:7]1[S:8][C:9]([C@@H:12]([NH2:17])[C:13]([F:16])([F:14])[F:15])=[CH:10][CH:11]=1)[CH2:5][O:6][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH:32]=[CH2:33]

Participants

7

Reactant 5

HCID 18052Allyl chloroformateHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 117628552HCID 117628552, compound

Product 1

HCID 131733462HCID 131733462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-amino-2-{5-[(1S)-1-amino-2,2,2-trifluoroethyl]thiophen-2-yl}ethanol dihydrochloride salt (2.78 g, 8.88 mmol) in dichloromethane (49 mL) cooled to 0° C. was added Hunig's base (9.3 mL), 53.3 mmol). Allyl chloroformate (0.95 mL, 8.88 mmol) was then added and the mixture was stirred overnight at room temperature. t-butyldimethylsilylchloride (4.0 g, 26.6 mmol) and dimethylaminopyridine (0.11 g, 0.89 mmol) were then added to the solution and the solution was stirred overnight. Solvent was removed by evaporation and the resulting crude mixture was purified on silica eluting with 10% to 60% ethyl acetate in hexane to give the title compound as a colorless oil. MS: m/z=460.5 (MNa+).

Workup

  1. stirringthe solution was stirred overnight
  2. customSolvent was removed by evaporation
  3. customthe resulting crude mixture was purified on silica eluting with 10% to 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5446fc0a76614bd3b60433d1e5e000e5
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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