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

HRID 398271노트

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HRID 398271 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-66f5c11c50f842eb99b5c6b3801aae76
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610734B2

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