Carbonocyanidic acid, methyl ester → (4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)-1-tritylpiperidin-4-yl)methanol

HRID 241648노트

반응식

HRID 241648 반응식
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:19][CH2:18]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].C([C:57](OC)=[O:58])#N>O1CCCC1>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]4([CH2:57][OH:58])[CH2:18][CH2:19][N:20]([C:23]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH2:21][CH2:22]4)(=[O:15])=[O:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 28660Carbonocyanidic acid, methyl esterHCID 2724682Lithium diisopropylamideHCID 585135841-(cyclopropylmethyl)-2-neopentyl-5-(1-tritylpiperidin-4-ylsulfonyl)-1H-benzo[d]imidazole

생성물 1

HCID 58513617(4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)-1-tritylpiperidin-4-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

To a solution of 1-(cyclopropylmethyl)-2-neopentyl-5-(1-tritylpiperidin-4-ylsulfonyl)-1H-benzo[d]imidazole (STEP E, 2.05 g, 3.24 mmol) in tetrahydrofuran (60 mL) at −60° C. was added lithium diisopropylamide (1.8 mol/L heptane/tetrahydrofuran/ethylbenzene solution, 2.34 mL, 4.22 mmol). After the mixture was warmed up to −40° C. over a period of 20 min and then stirred for 40 min at the same temperature, methyl cyanoformate (828 mg, 9.73 mmol) in tetrahydrofuran (3 mL) was added to the mixture. The mixture was stirred at 0° C. for 1.5 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate, gradient) to give 4:1 mixture of the title compound and the starting material (2.15 g).

후처리

  1. additionwas added to the mixture
  2. customThe reaction was quenched with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate, gradient)
  8. customto give

출처 및 근거

ORD 기록
ord-c6072575b2094ada9fec4dd23fae7ec2
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653063B2

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