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 1671742ノート

反応式

HRID 1671742 の反応式
[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

参加物

4

反応物 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

生成物 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 ester収率 145.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  1. customPurification on preparative reverse phase semi-prep column

出典と根拠

ORDレコード
ord-c790d7a5ccd04d83b6196df5e563f7e4
出典データセット
uspto-grants-2011_08
特許番号
US07994346B2

反応ノート

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