Dichloromethane → (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide

HRID 551520노트

반응식

HRID 551520 반응식
[CH3:1][CH2:2][NH:3][C:4]([CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@@H:12]1[C@@H:16](/[CH:17]=[CH:18]/[C@@H:19]([OH:28])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:15]([OH:29])[CH2:14][C@@H:13]1[OH:30])=[O:5].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C(Cl)Cl>O1CCOCC1>[CH3:1][CH2:2][NH:3][C:4]([CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@@H:12]1[C@@H:16](/[CH:17]=[CH:18]/[C:19]([CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:28])[C@H:15]([OH:29])[CH2:14][C@@H:13]1[OH:30])=[O:5]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 5311027Bimatoprost

생성물 1

HCID 35028392(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide수율 63.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
40 °C

실험 절차

A mixture of bimatoprost 1 (0.33 g, 0.8 mmol), DDQ (0.68 g, 3.0 mmol), CH2Cl2 (5 mL) and 1,4-dioxane (5 mL) was stirred for 24 h at 40° C. and evaporated in vacuo. The residue was purified by chromatography on a silica gel (20 g, eluent EtOAc then EtOAc/MeOH 20:1) to give 0.21 g (63%) of 15-keto bimatoprost 1c as yellow oil.

후처리

  1. customevaporated in vacuo
  2. customThe residue was purified by chromatography on a silica gel (20 g, eluent EtOAc

출처 및 근거

ORD 기록
ord-741db9fb96e34b7a8564348d6d1a63f4
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947740B2

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