Triethylamine → HCID 86730143, compound

HRID 1850115Notes

Reaction equation

HRID 1850115 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[CH:5][CH:4]=1.CS([Cl:23])(=O)=O.C(N(CC)CC)C.CCOC(C)=O.CCCCCCC>C(Cl)Cl>[Cl:23][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21899848Ethylacetate heptaneHCID 86730142HCID 86730142, compound

Product 1

HCID 86730143HCID 86730143, compoundYield 47,077.602%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(4-(hydroxymethyl)phenyl)ethylcarbamate (503 mg, 2 mmol) in DCM (10 mL) was added methanesulfonyl chloride (275 mg, 2.4 mmol) and triethylamine (0.56 mL, 4 mmol). The solution was stirred for 16 h at room temperature then washed with water and brine. After separation, the organic phase was dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/heptane 0 to 80%) provided (S)-tert-butyl 1-(4-(chloromethyl)phenyl)ethylcarbamate as a white solid (254 g, 47.1% yield).

Workup

  1. washthen washed with water and brine
  2. customAfter separation
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1837c24a40344821b87b0934b11ed34e
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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