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

HRID 393489노트

반응식

HRID 393489 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6ac402ddbc2241eab25081adf65aa8cb
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06806365B2

반응 노트

불러오는 중…