Sodium Chloride → HCID 86635694, compound

HRID 598866Notes

Reaction equation

HRID 598866 reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].CCN(CC)CC.[Na+].[Cl-]>C(Cl)Cl>[CH3:24][S:25]([O:1][CH2:2][CH2:3][C@@H:4]([NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:23])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58941596HCID 58941596, compound

Product 1

HCID 86635694HCID 86635694, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-tert-Butyl 4-hydroxy-1-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate was dissolved in 60 mL DCM and cooled to 0° C. MsCl (773 mL, 10 mmol) and Et3N (1.67 mL, 12 mmol) were added and the reaction was stirred for 1.5 hours at 0° C. NaCl (saturated, aqueous) was added, and the mixture was extracted with DCM (3×100 mL), dried over MgSO4 and evaporated. The title compound was obtained as an off-white solid and used without further purification in the next step. LCMS (API-ES) m/z (%): 411.1 (100%, M++H).

Workup

  1. extractionthe mixture was extracted with DCM (3×100 mL)
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-dcc49c4343ca487bbc35d2f0391b15b1
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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