Lithium hydroxide, monohydrate → (3S*,4R*)-3-{[(2-carboxy-2-methyl-propoxycarbonyl)-cyclopropyl-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158414노트

반응식

HRID 1158414 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][N:35]([CH:47]2[CH2:49][CH2:48]2)[C:36]([O:38][CH2:39][C:40]([C:43]([O:45]C)=[O:44])([CH3:42])[CH3:41])=[O:37])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>O.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:32])[CH3:33])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][N:35]([C:36]([O:38][CH2:39][C:40]([C:43]([OH:45])=[O:44])([CH3:42])[CH3:41])=[O:37])[CH:47]2[CH2:48][CH2:49]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 68616980(3S*,4R*)-3-{[Cyclopropyl-(2-methoxycarbonyl-2-methyl-propoxycarbonyl)-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 68617188(3S*,4R*)-3-{[(2-carboxy-2-methyl-propoxycarbonyl)-cyclopropyl-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of (3S*,4R*)-3-{[cyclopropyl-(2-methoxycarbonyl-2-methyl-propoxycarbonyl)-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (290 mg, 0.42 mmol) and LiOH•H2O (44 mg, 1.05 mmol) in H2O (2 mL) and THF (6 mL) is stirred at RT for 3 d. After evaporation of the solvent 1N HCl is added and the mixture is extracted with ethyl acetate. Drying (Na2SO4) of the combined extracts, filtration and evaporation of the solvent affords the title compound which is used without further purification. MS (LC-MS): 578.0 [M+H-Boc]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H20/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 5.44 min.

후처리

  1. customAfter evaporation of the solvent 1N HCl
  2. additionis added
  3. extractionthe mixture is extracted with ethyl acetate
  4. customDrying
  5. filtration(Na2SO4) of the combined extracts, filtration and evaporation of the solvent

출처 및 근거

ORD 기록
ord-fa6d1bae729043b3b4cde4e23e428a1e
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807709B2

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