Trimethylamine → 3-{2-[2-hydroxy-1-(3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy]acetoxy}propionic acid

HRID 1053551

반응식

HRID 1053551 반응식
[OH:1][CH:2]1[CH:19]([CH2:20][CH2:21][CH:22]([O:28]C2CCCCO2)[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.O[CH2:36][CH2:37][C:38]([O:40]CC1C=CC=CC=1)=[O:39].CN(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl.CC(OC)(C)C>[OH:1][CH:2]1[CH:19]([CH2:20][CH2:21][CH:22]([OH:28])[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]([O:18][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[O:17])[CH:10]=[CH:9][CH:8]=3

참가 물질

7

반응물 4

HCID 1146TrimethylamineHCID 84459Propanoic acid, 3-hydroxy-, phenylmethyl esterHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 90281645HCID 90281645, 화합물

생성물 1

HCID 1214807453-{2-[2-hydroxy-1-(3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy]acetoxy}propionic acid

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 15413tert-Butyl methyl ether용매

실험 절차

To a solution of Compound B (120 mg, 0.25 mmol), benzyl 3-hydroxypropionate (54 mg, 0.30 mmol) and trimethylamine (140 μL, 1.0 mmol) in DCM (4 mL) was added BOP—Cl (95 mg, 0.38 mmol). The reaction mixture was stirred at RT for 16 hr under nitrogen, diluted with MTBE, washed with brine, dried over sodium sulfate, and concentrated to an oil that was purified by silica gel chromatography. A solution of the THP-protected diester in ethanol (4 mL) was treated with PPTS (50 mg), stirred at 50° C. for 4 hr, and concentrated to an oil that was purified by silica gel chromatography. A solution of the THP-deprotected diester in dioxane (5 mL) was treated with wet 5% Pd/C (20 mg) and stirred for 24 hr under a balloon of hydrogen. The reaction mixture was filtered and concentrated to give crude Compound II-4. MS: m/z 485 [M+Na]+

후처리

  1. washwashed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to an oil that
  4. customwas purified by silica gel chromatography
  5. additionA solution of the THP-protected diester in ethanol (4 mL) was treated with PPTS (50 mg)
  6. stirringstirred at 50° C. for 4 hr
  7. concentrationconcentrated to an oil that
  8. customwas purified by silica gel chromatography
  9. additionA solution of the THP-deprotected diester in dioxane (5 mL) was treated with wet 5% Pd/C (20 mg)
  10. stirringstirred for 24 hr under a balloon of hydrogen
  11. filtrationThe reaction mixture was filtered
  12. concentrationconcentrated
  13. customto give crude Compound II-4

출처 및 근거

ORD 기록
ord-99aa46029a874eeaa0d37620c04c9656
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394227B1

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