Pyridine → HCID 86597131, compound

HRID 1984821Notes

Reaction equation

HRID 1984821 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([CH2:24][OH:25])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([Cl:23])[CH:17]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:27][S:28](Cl)(=[O:30])=[O:29].N1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([NH:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([Cl:23])[CH:17]=2)=[CH:12][CH:11]=1)[CH2:24][O:25][S:28]([CH3:27])(=[O:30])=[O:29])=[O:26])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 68867931HCID 68867931, compound

Product 1

HCID 86597131HCID 86597131, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[2-(3′-Chloro-4′-fluoro-biphenyl-4-yl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester (0.78 g, 2.05 mmol) was treated with methanesulfonyl chloride (0.235 g, 2.05 mmol) and pyridine (0.49 g, 6.15 mmol) in 5 mL of anhydrous dichloromethane at 0° C. The reaction mixture was allowed to come to room temperature and stirred for 4 h. The reaction mixture was diluted with 10 mL of dichloromethane and washed with water, brine and dried over Na2SO4. Solvent was removed under reduced pressure and silica gel column chromatography (CH2Cl2:MeOH) gave methanesulfonic acid 2-tert-butoxycarbonylamino-3-(3′-chloro-4′-fluoro-biphenyl-4-yl)-propyl ester (0.71 g).

Workup

  1. customto come to room temperature
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed under reduced pressure and silica gel column chromatography (CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-ce6babd00a724b85a573a5fd5cb8dd0c
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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