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 1944921Notes

Reaction equation

HRID 1944921 reaction equation
[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

Participants

5

Reactant 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

Product 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 acidYield 89.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-c2e21407c62f40b5abd727416d2566ad
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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