Sodium Hydroxide → (S)-3-[4-(2,6-Dichloro-benzoylamino)-phenyl]-2-{[1-(2-methoxy-ethyl)-cyclopentanecarbonyl]-amino}-propionic acid

HRID 393489ノート

反応式

HRID 393489 の反応式
C[O:2][C:3](=[O:35])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:34])=[O:26])=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[OH-].[Na+]>C(O)C.O1CCCC1>[Cl:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:34])[C:27]=1[C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C@@H:4]([C:3]([OH:35])=[O:2])[NH:5][C:6]([C:8]2([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:19][CH:20]=1)=[O:26]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 539042644-[[(2,6-Dichlorophenyl)Carbonyl]Amino]-N-[[1-(2-Methoxyethyl)-Cyclopentyl]Carbonyl]-L-Phenylalanine Methyl Ester

生成物 1

HCID 10196018(S)-3-[4-(2,6-Dichloro-benzoylamino)-phenyl]-2-{[1-(2-methoxy-ethyl)-cyclopentanecarbonyl]-amino}-propionic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a suspension of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-(2-methoxyethyl)-cyclopentyl]carbonyl]-L-phenylalanine methyl ester (20.17 mmol, 10.52 g) in ethanol (80 mL) and tetrahydrofuran (10 mL) was added aqueous 1.0 N sodium hydroxide (80 mL) at room temperature. The mixture was heated to 50° C. and the resulting clear solution was stirred overnight. Then, the ethanol solution was concentrated and diluted with 50 mL of water and was extracted with 200 mL of ether to remove neutral impurities. The aqueous layer was acidified with 1N HCl and the precipitated white solid was collected by filtration and washed with 200 mL of water and 200 mL of hexane. After air-drying, 8.4 g (82%) of as a white solid: mp 136-140° C. was obtained. 1H NMR, DMSO-d6 (400 MHz) δ 10.64 (s, 1H), 7.73 (d, 1H, J=22 Hz), 7.46-7.59 (m, 5H), 7.22 (d, 2H, J=22 Hz), 4.43-4.48 (m, 1H), 2.87-3.11 (m, 7H), 1.76-2.01 (m, 4H), 1.23-1.47 (m, 6H). HR MS (C25H28Cl2N2O5): Obs. mass, 507.1464. Calcd. mass, 507.1454 (M+H).

後処理

  1. concentrationThen, the ethanol solution was concentrated
  2. additiondiluted with 50 mL of water
  3. extractionwas extracted with 200 mL of ether
  4. customto remove neutral impurities
  5. filtrationthe precipitated white solid was collected by filtration
  6. washwashed with 200 mL of water and 200 mL of hexane
  7. customAfter air-drying
  8. custom8.4 g (82%) of as a white solid: mp 136-140° C. was obtained

出典と根拠

ORDレコード
ord-6ac402ddbc2241eab25081adf65aa8cb
出典データセット
uspto-grants-2004_10
特許番号
US06806365B2

反応ノート

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