Lithium hydroxide, monohydrate → 2-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]formamido}acetic acid

HRID 422183ノート

反応式

HRID 422183 の反応式
[OH:1][C:2]1[CH:19]=[C:18]([C:20]([NH:22][CH2:23][C:24]([O:26]C)=[O:25])=[O:21])[CH:17]=[C:16]2[C:3]=1[C@@:4]1([CH3:33])[C@H:13]([CH2:14][S:15]2(=[O:29])=[O:28])[C@:12]2([CH3:30])[C@H:7]([C:8]([CH3:32])([CH3:31])[CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5]1.O[Li].O>CO.O>[OH:1][C:2]1[CH:19]=[C:18]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])[CH:17]=[C:16]2[C:3]=1[C@@:4]1([CH3:33])[C@H:13]([CH2:14][S:15]2(=[O:29])=[O:28])[C@:12]2([CH3:30])[C@H:7]([C:8]([CH3:32])([CH3:31])[CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5]1

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 58294834methyl 2-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]formamido}acetate

生成物 1

HCID 532409462-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]formamido}acetic acid収率 84%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of methyl 2-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]-formamido}acetate (92) (0.07 g, 0.2 mmol) and LiOH.H2O (0.07 g, 2 mmol) in MeOH (10 mL) and water (2.0 mL) was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure, the aqueous residue was acidified with 1 M HCl and the resulting solid was collected by filtration to give 2-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]formamido}acetic acid (93) (0.057 g, 84%) as a pale brown solid. 1H NMR (CD3OD): δ 7.79 (d, 1H), 7.43 (d, 1H), 4.07 (s, 2H), 3.60 (d, 1H), 3.38 (m, 2H), 2.26 (d, 1H), 1.86-1.16 (m, 12H), 1.10-1.00 (m, 5H), 0.90 (s, 3H), 0.88 (s, 3H). MS m/z 462 (C24H33NO6S−H+).

後処理

  1. concentrationThe reaction 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-d01bb4d9219148c8b3f3f91510200263
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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