Hydrochloric Acid → Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-, methyl ester

HRID 1671742노트

반응식

HRID 1671742 반응식
[OH:1][C@H:2]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)/[CH:3]=[CH:4]/[C:5]#[C:6]/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C@H:11]1[O:15]C(C)(C)[O:13][C@H:12]1[CH2:18][O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].Cl>CO>[F:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][CH2:25][C@@H:2]([OH:1])/[CH:3]=[CH:4]/[C:5]#[C:6]/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C@@H:11]([OH:15])[C@@H:12]([OH:13])[CH2:18][O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:28][CH:29]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 865940532-[[(4S,5R)-5-[(1E,3E,7E,9S)-9-hydroxy-10-(4-fluorophenoxy)-1,3,7-decatrien-5-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester

생성물 1

HCID 9823441Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-, methyl ester수율 145.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 2-[[(4S,5R)-5-[(1E,3E,7E,9S)-9-hydroxy-1 0-(4-fluorophenoxy)-1,3,7-decatrien-5-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester, (1.1 g, 1.8 mmol) in methanol (25 mL) was treated with 1 mL of 1 N hydrochloric acid and the reaction was stirred for 2 days. The pH of the reaction was adjusted to neutrality. Purification on preparative reverse phase semi-prep column using a gradient of acetonitrile in water yielded 1.1 g of (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-1 1-ynoic acid, methyl ester, as an oil; 1H NMR (CDCl3) δ3.67 (m, 2H), 3.75 (s, 3H), 3.83 (m, 1H), 3.95 (m, 1H), 4.13 (m, 2H), 4.37 (m, 1H), 4.58 (m, 1H), 5.73 (dd, 1H), 5.86 (dd, 1H), 6.04 (dt, 1H), 6.17 (m, 1H), 6.40 (m, 1H), 6.58 (m, 1H), 6.9 (m, 4H) ppm.

후처리

  1. customPurification on preparative reverse phase semi-prep column

출처 및 근거

ORD 기록
ord-c790d7a5ccd04d83b6196df5e563f7e4
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994346B2

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