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

HRID 398271ノート

反応式

HRID 398271 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-66f5c11c50f842eb99b5c6b3801aae76
出典データセット
uspto-grants-2003_08
特許番号
US06610734B2

反応ノート

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