Benzyl Alcohol → {2-hydroxy-1-[3-(tetrahydropyran-2-yloxy)octyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy}acetic acid benzyl ester

HRID 1053550

반응식

HRID 1053550 반응식
[OH:1][CH:2]1[CH:19]([CH2:20][CH2:21][CH:22]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:5]2[CH2:6][C:7]3[C:12]([CH2:13][CH:4]2[CH2:3]1)=[C:11]([O:14][CH2:15][C:16]([OH:18])=[O:17])[CH:10]=[CH:9][CH:8]=3.[CH2:35](O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl.COC(C)(C)C>[CH2:35]([O:17][C:16](=[O:18])[CH2:15][O:14][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH2:13][CH:4]1[CH2:3][CH:2]([OH:1])[CH:19]([CH2:20][CH2:21][CH:22]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:5]1[CH2:6]2)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 90281645{2-hydroxy-1-[3-(tetrahydropyran-2-yloxy)octyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy}acetic acid2회

생성물 1

HCID 121480749{2-hydroxy-1-[3-(tetrahydropyran-2-yloxy)octyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy}acetic acid benzyl ester

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 15413tert-Butyl methyl ether용매

실험 절차

A solution of {2-hydroxy-1-[3-(tetrahydropyran-2-yloxy)octyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy}acetic acid (Compound B) (2 g, 4.21 mmol), benzyl alcohol (2.47 g, 22.9 mmol) and triethylamine (7.2 g, 71.3 mmol) in dichloromethane (DCM) (20 mL) was treated with bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP—Cl) (7.8 g, 30.7 mmol) at 0° C. and stirred at room temperature (RT) for 2 hr. The reaction mixture was diluted with methyl-tert-butyl ether (MTBE) and washed with water and then brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography to provide Compound C. MS: m/z 587 [M+Na]+

후처리

  1. washwashed with water
  2. dry with materialbrine, dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-c97958e20147431792fafb6122448452
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394227B1

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