Methanesulfonyl chloride → HCID 86705550, compound

HRID 2279565Notes

Reaction equation

HRID 2279565 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1.CCOC(C)=O>[CH3:21][S:22]([O:12][CH2:11][CH2:10][C@@H:9]([NH:13][C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20])[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:24])=[O:23]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 27281741HCID 27281741, compound

Product 1

HCID 86705550HCID 86705550, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 174 (1.327 g, 4.144 mmol) in THF (30 mL) at 0° C. was added TEA (0.6931 mL, 4.973 mmol) and MsCl (0.3528 mL, 4.559 mmol) and the solution stirred for 1 h at 0° C. The mixture was diluted with EtOAc, washed with dilute HCl solution, aq. satd. NaHCO3, and brine, dried (MgSO4) and concentrated to afford 1.51 grams (91%) of (R)-3-(tert-butoxycarbonylamino)-3-(3,4-dichlorophenyl)propyl methanesulfonate (364). The product may contain some of the corresponding chloride.

Workup

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

Sources & evidence

ORD record
ord-cf8349f9eec944efa22707530bbfe79e
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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