5-Chlorothiophene-2-sulfonyl chloride → HCID 68429355, compound

HRID 2266894Notes

Reaction equation

HRID 2266894 reaction equation
[NH2:1][CH:2]([CH:6]1[CH2:11][CH2:10][C:9]([F:13])([F:12])[CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4].[Cl:14][C:15]1[S:19][C:18]([S:20](Cl)(=[O:22])=[O:21])=[CH:17][CH:16]=1>[OH-].[Na+].C1COCC1>[Cl:14][C:15]1[S:19][C:18]([S:20]([NH:1][CH:2]([CH:6]2[CH2:11][CH2:10][C:9]([F:12])([F:13])[CH2:8][CH2:7]2)[C:3]([OH:5])=[O:4])(=[O:22])=[O:21])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 45027014HCID 45027014, compound

Product 1

HCID 68429355HCID 68429355, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

The amino(4,4-difluorocyclohexyl)acetic acid (2.68 g, 10.973 mmol) was dissolved in 2N NaOH (20 mL). The solution was cooled to 0° C., 5-chlorothiophene-2-sulfonyl chloride (3.25 g, 12.42 mmol) was added (5 min) dropwise as a solution in THF (10 mL). The solution was allowed to warm up to 25° C. overnight. After 19 h, THF was removed in vacuo and the mixture was acidified to a pH of about 1 to about 2 with 2N HCl (20 mL). The aqueous layer was washed with EtOAc (4×50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated to produce {[(5-chlorothien-2-yl)sulfonyl]amino}(4,4-difluorocyclohexyl)acetic acid as a crude oil (3.8 g, 98.2%). Mass Spectrum (−ESI): 372 (M−H)−.

Workup

  1. temperatureto warm up to 25° C. overnight
  2. customTHF was removed in vacuo
  3. washThe aqueous layer was washed with EtOAc (4×50 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d82612ceff554b8b8e45d61c62020e59
Source dataset
uspto-grants-2010_12
Patent number
US07858658B2

Reaction notes

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