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

HRID 2062309Notes

Reaction equation

HRID 2062309 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-20d833bfbed8430a9d35d4228110c503
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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