Hydrochloric Acid → (3-{(S)-2-([R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)acetic acid

HRID 2412257Notes

Reaction equation

HRID 2412257 reaction equation
C[O:2][C:3](=[O:44])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][C@@H:12]([NH:14][CH2:15][C@@H:16]([C:25]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:31]3[C:26]=2[CH:27]=[CH:28][C:29](=[O:43])[NH:30]3)[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH3:13])[CH:6]=1.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH2:36]([O:35][C:32]1[CH:33]=[CH:34][C:25]([C@@H:16]([O:17][Si:18]([C:21]([CH3:22])([CH3:24])[CH3:23])([CH3:20])[CH3:19])[CH2:15][NH:14][C@@H:12]([CH3:13])[CH2:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:44])=[O:2])[CH:10]=[CH:9][CH:8]=2)=[C:26]2[C:31]=1[NH:30][C:29](=[O:43])[CH:28]=[CH:27]2)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66773664(3-{(S)-2-[(R)-2-(8-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)acetic Acid Methyl Ester

Product 1

HCID 66770367(3-{(S)-2-([R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)acetic acidYield 39.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of (3-{(S)-2-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)acetic acid methyl ester (810 mg, 1.3 mmol) in a 3:2:1 mixture of THF/MeOH/water (4 mL) was added lithium hydroxide (158 mg, 6.59 mmol). The resulting mixture was stirred at room temperature for 3 hours and then acidified to pH 6 with concentrated aqueous hydrochloric acid. This mixture was concentrated under reduced pressure to give a yellow solid (307 mg, 39% yield), which was used in the next reaction without further purification.

Workup

  1. concentrationThis mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8517e5dae90e4c74b9afd22d4a9e464b
Source dataset
uspto-grants-2014_08
Patent number
US08816088B2

Reaction notes

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