Triethylamine → HCID 86602053, compound

HRID 1295369Notes

Reaction equation

HRID 1295369 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:32])[C:16]([N:18]2[CH2:23][CH:22]3[C@@:20]([CH2:24][OH:25])([CH2:21]3)[C@@H:19]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C(Cl)Cl>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]([N:15]([CH3:32])[C:16]([N:18]2[CH2:23][CH:22]3[C@@:20]([CH2:24][O:25][S:43]([CH3:42])(=[O:45])=[O:44])([CH2:21]3)[C@@H:19]2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:17])[CH3:14])[CH:4]=[C:3]([C:2]([F:1])([F:33])[F:34])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86602054HCID 86602054, compound

Product 1

HCID 86602053HCID 86602053, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 35, 4 isomers, one being (1S,2S)-1-Hydroxymethyl-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid [(R)-1-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methyl-amide (0.28 g, 0.57 mmol) and triethylamine (0.13 mL, 0.96 mmol) in methylene chloride (6 mL) at 0° C. was added methanesulfonyl chloride (0.06 mL, 0.79 mmol). The reaction was allowed to warm to room temperature and stir for 2 hours. The reaction was washed with cold 0.5N HCl and the phases separated. The methylene chloride was washed with cold 0.5N NaOH, washed with brine, and dried over sodium sulfate, filtered and concentrated to give the title compound as a pink foam (0.32 g, quantitative yield). This material was processed without further purification.

Workup

  1. washThe reaction was washed with cold 0.5N HCl
  2. customthe phases separated
  3. washThe methylene chloride was washed with cold 0.5N NaOH
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6d87bfc0ed444805af900cd0226fef80
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

Loading…