5-[5-(Trifluoromethyl)-1,2-oxazol-3-yl]thiophene-2-sulfonyl chloride → HCID 86607500, compound

HRID 898858Notes

Reaction equation

HRID 898858 reaction equation
Cl.[CH3:2][O:3][N:4]([CH3:20])[C:5]([C@@:7]1([NH2:19])[C@@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:8]1[CH2:16][O:17][CH3:18])=[O:6].[F:21][C:22]([F:38])([F:37])[C:23]1[O:27][N:26]=[C:25]([C:28]2[S:32][C:31]([S:33](Cl)(=[O:35])=[O:34])=[CH:30][CH:29]=2)[CH:24]=1>N1C=CC=CC=1>[CH3:2][O:3][N:4]([CH3:20])[C:5]([C@@:7]1([NH:19][S:33]([C:31]2[S:32][C:28]([C:25]3[CH:24]=[C:23]([C:22]([F:21])([F:37])[F:38])[O:27][N:26]=3)=[CH:29][CH:30]=2)(=[O:34])=[O:35])[C@@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:8]1[CH2:16][O:17][CH3:18])=[O:6]

Participants

4

Reactant 2

HCID 27775265-[5-(Trifluoromethyl)-1,2-oxazol-3-yl]thiophene-2-sulfonyl chlorideHCID 86607501HCID 86607501, compound

Product 1

HCID 86607500HCID 86607500, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The (1R*,2R*,3R*)-1-amino-2-methoxymethyl-3-phenyl-cyclopropanecarboxylic acid methoxy-methyl-amide hydrochloride (22 mg, 0.082 mmol) was dissolved in 1 mL of pyridine. To this solution was added 5-(5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-sulfonyl chloride (25 mg, 0.079 mmol) and the mixture was stirred at room temperature overnight. After concentration, the reaction mixture was diluted with EtOAc and washed with sat. NaHCO3 (2×) and brine. After drying over MgSO4, the solution was concentrated and purified using prep-TLC (1:1 hexanes/EtOAc) to afford 13 mg of the desired product (32%).

Workup

  1. concentrationAfter concentration
  2. additionthe reaction mixture was diluted with EtOAc
  3. washwashed with sat. NaHCO3 (2×) and brine
  4. dry with materialAfter drying over MgSO4
  5. concentrationthe solution was concentrated
  6. custompurified

Sources & evidence

ORD record
ord-34397c6923d34b00b162eed98d7d1539
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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