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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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Lithium hydroxide, monohydrate → (2R,6S,13aS,14aR,16aS,Z)-2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-(butylthio)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylic acid

HRID 1666533
ノート
印刷プレビュー

反応式

HRID 1666533 の反応式
[C:1]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([S:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:40][N:10]3[C:11](=[O:39])[C@@H:12]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][C@@H:20]4[CH2:25][C@@:21]4([C:26]([O:28]CC)=[O:27])[NH:22][C:23](=[O:24])[C@@H:9]3[CH2:8]2)=[CH:3][CH:2]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[C:1]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:2]=[CH:3][C:4]([C@@:7]2([S:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:40][N:10]3[C:11](=[O:39])[C@@H:12]([NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][C@@H:20]4[CH2:25][C@@:21]4([C:26]([OH:28])=[O:27])[NH:22][C:23](=[O:24])[C@@H:9]3[CH2:8]2)=[CH:5][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 168937Lithium hydroxide, monohydrate3 回HCID 57988332(2R,6S,13aS,14aR,16aS,Z)-ethyl 2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-(butylthio)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate

生成物 1

HCID 57988333(2R,6S,13aS,14aR,16aS,Z)-2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-(butylthio)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylic acid
収率 90.2%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒3 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2R,6S,13aS,14aR,16aS,Z)-ethyl 2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-(butylthio)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (59 mg, 0.082 mmol) in THF (1 mL) and MeOH (1.000 mL) was added pre-made solution of Lithium hydroxide monohydrate (6.90 mg, 0.164 mmol) in water (1 mL). The resulting cloudy solution was stirred at room for 5 h. LC/MS analysis showed partial reaction. Another portion of Lithium hydroxide monohydrate (6.90 mg, 0.164 mmol) in water (0.2 ml) was added and stirred for additional 17 hours. LC/MS analysis showed there was still small portion of starting material remained. Another portion of Lithium hydroxide monohydrate (6.90 mg, 0.164 mmol) in water (0.2 ml) was added and stirred for additional 5 hours. Quenched with 5% citric acid, extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to afford the desired product (2R,6S,13aS,14aR,16aS,Z)-2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-(butylthio)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylic acid (57 mg, 0.074 mmol, 90% yield) as a white foam. 1H NMR (500 MHz, MeOD) δ ppm 0.84 (t, J=7.32 Hz, 3 H) 1.14-1.37 (m, 5 H) 1.38-1.54 (m, 16 H) 1.53-1.68 (m, 4 H) 1.82-1.95 (m, 1 H) 1.96-2.12 (m, 1 H) 2.21-2.38 (m, 2 H) 2.42 (dt, J=12.21, 7.17 Hz, 1 H) 2.48-2.63 (m, 1 H) 2.84-3.00 (m, 1 H) 3.92-4.18 (m, 2 H) 4.49 (dd, J=10.38, 2.75 Hz, 1 H) 5.18 (d, J=10.68 Hz, 1 H) 5.35 (t, J=9.77 Hz, 1 H) 5.56-5.68 (m, 1 H) 7.30-7.39 (m, 1 H) 7.45 (t, J=7.63 Hz, 2 H) 7.55-7.63 (m, 4 H) 7.77 (d, J=8.24 Hz, 2 H). LC-MS (retention time: 3.34 min, method C), MS m/z 690(M+H).

後処理

  1. customreaction
  2. stirringstirred for additional 17 hours
  3. stirringstirred for additional 5 hours
  4. customQuenched with 5% citric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-da95846156684f9cb1f0fed81d0926b8
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08044023B2

反応ノート

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