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

HRID 2062354Notes

Reaction equation

HRID 2062354 reaction equation
[CH2:1]([O:6][C:7](=[O:33])[NH:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][N:12]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[N:18]=[C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[OH:32])[N:16]=2)[CH2:11]1)[C:2]([CH3:5])([CH3:4])[CH3:3].[ClH:34].CCOCC>C(Cl)Cl>[ClH:34].[OH:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:17]1[N:16]=[C:15]([N:12]2[CH2:13][CH2:14][C@@H:10]([CH2:9][NH:8][C:7](=[O:33])[O:6][CH2:1][C:2]([CH3:3])([CH3:4])[CH3:5])[CH2:11]2)[C:24]2[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=2)[N:18]=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-f72da48263db418487646d10b17befb5
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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