Methanesulfonyl chloride → HCID 131733488, compound

HRID 2279576Notes

Reaction equation

HRID 2279576 reaction equation
[F:1][CH:2]([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl.CCOC(C)=O>[CH3:23][S:24]([O:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:21])[C:7]1[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:22])[F:1])=[CH:9][CH:8]=1)(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86705562HCID 86705562, compound

Product 1

HCID 131733488HCID 131733488, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 386 (550 mg, 1.73 mmol) in DCM (20 mL) at 0° C. was added TEA (290 μL, 2.08 mmol) and MeSO2Cl (148 μL, 1.91 mmol) and stirring was continued for 1 h at 0° C. The mixture was diluted with EtOAc, washed sequentially with water, dilute HCl solution, aq. satd. NaHCO3 and brine, dried (MgSO4), and concentrated to afford 685 mg (100%) of (R)-3-(tert-butoxycarbonylamino)-3-(4-(difluoromethoxy)phenyl)propyl methanesulfonate (388) containing some of the corresponding chloride.

Workup

  1. washwashed sequentially with water, dilute HCl solution, aq. satd
  2. dry with materialNaHCO3 and brine, dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8088d20c8f5a46eab16aed4e6107797d
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

Loading…