Hydrochloric Acid → (S)-tetrahydrofuran-3-yl(R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride

HRID 2079394Notes

Reaction equation

HRID 2079394 reaction equation
[ClH:1].CCOCC.[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:23]=[C:22]([N:24]2[CH2:28][CH2:27][C@@H:26]([NH:29][C:30](=[O:37])[O:31][C@H:32]3[CH2:36][CH2:35][O:34][CH2:33]3)[CH2:25]2)[C:21]2[C:16](=[CH:17][C:18]([CH3:38])=[CH:19][CH:20]=2)[N:15]=1>C(Cl)Cl>[ClH:1].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:23]=[C:22]([N:24]2[CH2:28][CH2:27][C@@H:26]([NH:29][C:30](=[O:37])[O:31][C@H:32]3[CH2:36][CH2:35][O:34][CH2:33]3)[CH2:25]2)[C:21]2[C:16](=[CH:17][C:18]([CH3:38])=[CH:19][CH:20]=2)[N:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 136121427(S)-tetrahydrofuran-3-yl (R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 136412254(S)-tetrahydrofuran-3-yl(R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.0 M HCl solution in Et2O (192 μL, 0.38 mmol) was slowly added at −20° C. to a stirring solution of (S)-tetrahydrofuran-3-yl (R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (167 mg, 0.38 mmol) in 700 μL of CH2Cl2. The reaction was allowed to warm to room temperature and was stirred for 25 minutes. Solvents were removed under reduced pressure, and the residue was triturated with Et2O and filtered to give (S)-tetrahydrofuran-3-yl (R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride. LC/MS: m/z 435.2 (M+H)+ at 2.41 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customSolvents were removed under reduced pressure
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-9bb3ce436a6340b2a920742de03c9919
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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