Sodium Hydroxide → Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-

HRID 2078509노트

반응식

HRID 2078509 반응식
[F:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][CH2:7][C@@H:8]([OH:28])/[CH:9]=[CH:10]/[C:11]#[C:12]/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C@@H:17]([OH:27])[C@@H:18]([OH:26])[CH2:19][O:20][CH2:21][C:22]([O:24]C)=[O:23])=[CH:4][CH:3]=1.[OH-].[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CO>[F:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][CH2:7][C@@H:8]([OH:28])/[CH:9]=[CH:10]/[C:11]#[C:12]/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C@@H:17]([OH:27])[C@@H:18]([OH:26])[CH2:19][O:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 9823441Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-, methyl ester

생성물 1

HCID 10111981Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-수율 90.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, methyl ester, (0.4 g, 0.95 mmol) in methanol (20 mL) was treated with 1 N NaOH (aq) (4 mL, 4 mmol) solution and shaken and allowed to stand for three hours. The reaction mixture was then treated with saturated potassium monophosphate and poured onto an HP20 column. Elution with a gradient of methanol in water gave 0.35 g of (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, which solidified upon standing; 1H NMR (CD3OD) δ 3.63 (m, 2H), 3.667 (m, 1H), 3.91 (m, 2H), 4.113 (s, 2H), 4.150, (t, 1H), 4.498, (m, 1H), 5.762 (dd, 1H), 5.953 (dd, 1H), 6.003 (dt, 1H), 6.202 (dd, 1H), 6.380 (dd, 1H), 6.596 (dd, 1H), 6.928 (m, 2H), 6.988 (m, 2H) ppm.

후처리

  1. additionpoured onto an HP20 column
  2. washElution with a gradient of methanol in water

출처 및 근거

ORD 기록
ord-faea792284de49ae9361d17593e7b5fd
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928255B2

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