Hydrochloric Acid → neopentyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochloride

HRID 2079438Notes

Reaction equation

HRID 2079438 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:22][CH2:21][C@@H:20]([CH2:23][NH:24][C:25](=[O:32])[O:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:33])=[CH:13][CH:14]=2)[N:9]=1.[ClH:34].CCOCC>C(Cl)Cl>[ClH:34].[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:22][CH2:21][C@@H:20]([CH2:23][NH:24][C:25](=[O:32])[O:26][CH2:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:33])=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121466neopentyl((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate

Product 1

HCID 136330122neopentyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of neopentyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate (215 mg, 0.48 mmol) in CH2Cl2 (2 ml) was stirred under an N2 atmosphere. A 1.0 M HCl solution in ether (0.48 ml, 0.48 mmol) was added dropwise to this solution. After 10 minutes, ether (8 ml) was added until a precipitate formed, which was filtered and dried to obtain neopentyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochloride (214 mg, 92%). LC/MS: m/z 449 (M+H)+ at 2.75 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customformed
  2. filtrationwhich was filtered
  3. customdried

Sources & evidence

ORD record
ord-b9a30e23e3d8437da4e797f8c13dfe61
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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