Water → [4-(Benzothiazole-2-carbonyl)-cyclohexyl]-carbamic acid tert-butyl ester

HRID 1012912

反応式

HRID 1012912 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li]CCCC.[C:15]([O:19][C:20](=[O:34])[NH:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([C:28](=[O:33])N(OC)C)[CH2:24][CH2:23]1)([CH3:18])([CH3:17])[CH3:16].O>C1COCC1>[C:15]([O:19][C:20](=[O:34])[NH:21][CH:22]1[CH2:23][CH2:24][CH:25]([C:28]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[O:33])[CH2:26][CH2:27]1)([CH3:18])([CH3:16])[CH3:17]

参加物

6

反応物 4

HCID 962WaterHCID 7222BenzothiazoleHCID 178418339ButyllithiumHCID 178502731HCID 178502731、化合物

生成物 1

HCID 67317166[4-(Benzothiazole-2-carbonyl)-cyclohexyl]-carbamic acid tert-butyl ester収率 82.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of benzothiazole (675 mg, 0.55 ml, 5 mmol) in THF (20 ml) at −78° C. was added dropwise n-BuLi (2.5M in Hex, 2 ml) such that the temperature did not exceed −70° C. The brown solution was stirred at this temperature for 15 min before dropwise addition of a solution of [trans-4-(methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (716 mg, 2.5 mmol, prepared according to WO 03/053933) in THF (2 ml). The temperature was kept below −70° C. The brown solution was then gradually allowed to reach RT (over 3 h). Mixture was poured into water and extracted with EtOAc. The combined organic extracts were washed with brine and dried over MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography over SiO2 (Hex/EtOAc 4:1 then DCM). The relevant fractions were pooled, evaporated under reduced pressure, digested with Hex and filtered to give 740 mg (82%) of [4-(benzothiazole-2-carbonyl)-cyclohexyl]-carbamic acid tert-butyl ester.

後処理

  1. customdid not exceed −70° C
  2. customwas kept below −70° C
  3. customto reach RT
  4. custom(over 3 h)
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography over SiO2 (Hex/EtOAc 4:1
  10. customevaporated under reduced pressure
  11. filtrationfiltered

出典と根拠

ORDレコード
ord-35a01e6be0c24725a8d37793c2468181
出典データセット
uspto-grants-2011_07
特許番号
US07981886B2

関連ノート

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