Tetrahydrofuran → (1R,10R,11S,16S)-3-methoxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid

HRID 422173ノート

反応式

HRID 422173 の反応式
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([C:21]([O-:23])=[O:22])[CH:18]=[C:17]2[C:4]=1[C@H:5]1[C@H:14]([CH2:15][S:16]2(=[O:25])=[O:24])[C@:13]2([CH3:26])[C@H:8]([C:9]([CH3:28])([CH3:27])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1.O[Li].O.[CH2:32]1COCC1>O>[CH3:1][O:2][C:3]1[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[C:17]2[C:4]=1[C@@:5]1([CH3:32])[C@H:14]([CH2:15][S:16]2(=[O:25])=[O:24])[C@:13]2([CH3:26])[C@H:8]([C:9]([CH3:28])([CH3:27])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86654190(1R,10S,11S,16S)-3-methoxy-11,15,15-trimethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylate

生成物 1

HCID 53240648(1R,10R,11S,16S)-3-methoxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid収率 98%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of (1R,10S,11S,16S)-3-methoxy-11,15,15-trimethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylate (59) (0.29 g, 0.66 mmol) and LiOH.H2O (0.08 g, 3.3 mmol) in THF (15 mL) and water (5.0 mL) was stirred at room temperature for 18 h. The mixture was concentrated under reduced pressure and the residue was acidified with 1 M HCl. The resulting solid was collected by filtration to give (1R,10R,11S,16S)-3-methoxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid (80) (0.27 g, 98%) as a white solid. 1H NMR (CD3OD): δ 8.04 (d, 1H), 7.74 (d, 1H), 3.94 (s, 3H), 3.47-3.35 (m, 3H), 2.26 (d, 1H), 1.86-1.16 (m, 11H), 1.10-1.00 (m, 5H), 0.89 (s, 3H), 0.87 (s, 3H). MS m/z 421 (O23H32O5S+H+).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. filtrationThe resulting solid was collected by filtration

出典と根拠

ORDレコード
ord-8f4f1754d415413ab5f6fb60ef090896
出典データセット
uspto-grants-2012_01
特許番号
US08101605B2

反応ノート

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