Lithium hydroxide, monohydrate → 1-{[(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]carbonyl}piperidine-4-carboxylic acid

HRID 422188ノート

反応式

HRID 422188 の反応式
[OH:1][C:2]1[CH:19]=[C:18]([C:20]([N:22]2[CH2:27][CH2:26][CH:25]([C:28]([O:30]C)=[O:29])[CH2:24][CH2:23]2)=[O:21])[CH:17]=[C:16]2[C:3]=1[C@@:4]1([CH3:37])[C@H:13]([CH2:14][S:15]2(=[O:33])=[O:32])[C@:12]2([CH3:34])[C@H:7]([C:8]([CH3:36])([CH3:35])[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]([N:22]2[CH2:27][CH2:26][CH:25]([C:28]([OH:30])=[O:29])[CH2:24][CH2:23]2)=[O:21])[CH:17]=[C:16]2[C:3]=1[C@@:4]1([CH3:37])[C@H:13]([CH2:14][S:15]2(=[O:33])=[O:32])[C@:12]2([CH3:34])[C@H:7]([C:8]([CH3:36])([CH3:35])[CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5]1

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 58294858methyl 1-{[(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]carbonyl}piperidine-4-carboxylate

生成物 1

HCID 532409481-{[(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]carbonyl}piperidine-4-carboxylic acid収率 64.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of methyl 1-{[(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]carbonyl}piperidine-4-carboxylate (97) (0.10 g, 0.18 mmol) and LiOH.H2O (0.10 g, 2.4 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 and acidified with 1 M HCl. The resulting solid was collected by filtration to give 1-{[(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]carbonyl}piperidine-4-carboxylic acid (98) (0.06 g, 63%) as a white solid. 1H NMR (CD3OD): δ 7.29 (d, 1H), 6.97 (d, 1H), 4.43 (m, 1H), 3.70 (m, 1H), 3.58 (m, 1H), 3.36 (m, 2H), 3.26-2.96 (m, 4H), 2.62 (m, 1H), 2.24 9d, 1H), 2.10-1.16 (m, 13H), 1.09-0.99 (m, 5H), 0.90 (s, 3H), 0.88 (s, 3H). MS m/z 516 (C28H39NO6S−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-0fd0516a95b6419a85d66fe6800cb4ec
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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