Ammonium Chloride → 5-Chloro-N-{(S,S)-1-[(S)-cyclohex-2-en-1-yl(hydroxy)methyl]-2-methylbutyl}thiophene-2-sulfonamide

HRID 398271Notes

Reaction equation

HRID 398271 reaction equation
[Mg].Br[C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1.[Cl:9][C:10]1[S:14][C:13]([S:15]([NH:18][C@H:19]([CH:24]=[O:25])[C@H:20]([CH2:22][CH3:23])[CH3:21])(=[O:17])=[O:16])=[CH:12][CH:11]=1.[NH4+].[Cl-]>C1COCC1>[Cl:9][C:10]1[S:14][C:13]([S:15]([NH:18][C@H:19]([C@H:24]([CH:8]2[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]2)[OH:25])[C@@H:20]([CH3:21])[CH2:22][CH3:23])(=[O:17])=[O:16])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5197751-Bromocyclohex-1-eneHCID 5462224MagnesiumHCID 590862015-Chloro-N-[(S,S)-1-formyl-2-methylbutyl]thiophene-2-sulfonamide

Product 1

HCID 590861825-Chloro-N-{(S,S)-1-[(S)-cyclohex-2-en-1-yl(hydroxy)methyl]-2-methylbutyl}thiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a two dram vial containing magnesium turnings (60 mg, 2.5 mmol) suspended in THF (3 mL) was added 2-bromocyclohexene (288 μL, 2.5 mmol) followed by 5-chlorothiophene-2-sulfonyl isoleucinal (1 mL of a 1 M THF solution, 1 mmol, example 118). The vial was capped and agitated at 50° C. for 18 h. The vial was cooled and sat. aqueous NH4Cl (1 mL) was added. The vial was vortexed and the organic layer was transferred into a tarred vial and the aqueous layer was extracted with EtOAc (1 mL). The combined organics were concentrated in vacuo and the residue was submitted to semipreparative RP-HPLC using the conditions below.

Workup

  1. customThe vial was capped
  2. temperatureThe vial was cooled
  3. extractionwas extracted with EtOAc (1 mL)
  4. concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-66f5c11c50f842eb99b5c6b3801aae76
Source dataset
uspto-grants-2003_08
Patent number
US06610734B2

Reaction notes

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