Hydrochloric Acid → (R)-3-(2-((2-(8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)amino)-2-methylpropyl)benzoic acid

HRID 1944921노트

반응식

HRID 1944921 반응식
[Li+].[OH-].[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C@@H:22]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:23][NH:24][C:25]([CH3:38])([CH3:37])[CH2:26][C:27]2[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=2)[C:30]([O:32]C)=[O:31])=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[CH:17]=[CH:16]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>C1COCC1.CO.O>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C@@H:22]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:23][NH:24][C:25]([CH3:38])([CH3:37])[CH2:26][C:27]2[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=2)[C:30]([OH:32])=[O:31])=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[CH:17]=[CH:16]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58505217(R)-Methyl 3-[2-[[2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-[(tert-butyldimethylsilyl)oxy]ethyl]amino]-2-methylpropyl]benzoate

생성물 1

HCID 58505082(R)-3-(2-((2-(8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)amino)-2-methylpropyl)benzoic acid수율 89.1%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

Solid LiOH (370 mg, 15.4 mmol) was added to a stirring solution of Intermediate 100 (950 mg, 1.55 mmol) in THF/MeOH/H2O (15 mL, 3/1/1) at rt. The reaction mixture was stirred over night then pH was adjusted to 1 with 1 N HCl. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude acid (1.09 g) as yellow solid. Recrystallization (CH2Cl2/Et2O) afforded the title compound (830 mg, 89%) as off white solid. ES/MS calcd. for C35H45N2O5Si+ 601.3. Found m/z=601.3 (M+H)+.

후처리

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give crude acid (1.09 g) as yellow solid
  6. customRecrystallization (CH2Cl2/Et2O)

출처 및 근거

ORD 기록
ord-c2e21407c62f40b5abd727416d2566ad
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394829B2

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