Triethylamine → Carbamic acid, N-[2,2,2-trifluoro-1-[[(methylsulfonyl)oxy]methyl]ethyl]-, phenylmethyl ester

HRID 878404Notes

Reaction equation

HRID 878404 reaction equation
[F:1][C:2]([F:18])([F:17])[CH:3]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][OH:5].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([O:5][CH2:4][CH:3]([NH:6][C:7]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:16])[C:2]([F:17])([F:18])[F:1])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23237021HCID 23237021, compound

Product 1

HCID 89486788Carbamic acid, N-[2,2,2-trifluoro-1-[[(methylsulfonyl)oxy]methyl]ethyl]-, phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl (1,1,1-trifluoro-3-hydroxypropan-2-yl)carbamate (300 g, 1.14 mol) in dichloromethane (2500 mL) were added triethylamine (128 g, 1.27 mol) and methanesulfonylchloride (144 g, 1.26 mol). After 2 hours, the reaction mixture was quenched with water (1000 mL) and extracted with dichloromethane (3×300 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2-{[(benzyloxy)carbonyl]amino}-3,3,3-trifluoropropyl methanesulfonate. The material was used without further purification.

Workup

  1. customthe reaction mixture was quenched with water (1000 mL)
  2. extractionextracted with dichloromethane (3×300 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb70de6f8e7647168d6cb288ed8632c0
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

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