Sulfuric Acid → (R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate sulfate

HRID 1693022Notes

Reaction equation

HRID 1693022 reaction equation
[OH:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:22]=[C:21]([N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:29](=[O:35])[O:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:24]2)[C:20]2[C:15](=[CH:16][C:17]([CH3:36])=[CH:18][CH:19]=2)[N:14]=1>C(#N)C.C1COCC1>[S:2]([OH:5])([OH:4])(=[O:3])=[O:1].[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:22]=[C:21]([N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:29](=[O:35])[O:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:24]2)[C:20]2[C:15](=[CH:16][C:17]([CH3:36])=[CH:18][CH:19]=2)[N:14]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 135771831(R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 136365375(R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate sulfate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 0.5 M solution of H2SO4 in acetonitrile (2.38 mL) was added to a solution of ((R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (0.5 g, 1.19 mmol) in dry THF (2.0 mL), and the reaction was stirred at RT for 2 h. The formed gelatinous white slurry was filtered, washed with THF, and dried under vacuum to give (R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate sulfate as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.29 (d, J=8.2 Hz, 1H), 8.15 (d, J=7.1 Hz, 1H), 7.76 (s, 1H), 7.61 (s, 1H), 7.55-7.51 (m, 2H), 7.12-7.04 (m, 2H), 4.40-4.02 (m, 4H), 3.98 (d, J=9.0 Hz, 1H), 3.84-3.75 (m, 2H), 2.54 (s, 3H), 2.27-2.22 (m, 1H), 2.10-2.08 (m, 1H), 1.98-1.79 (m, 1H), 0.88 (d, J=6.4 Hz, 6H) ppm. LC/MS: m/z 421.1 (M+H)+ at 2.71 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. filtrationThe formed gelatinous white slurry was filtered
  2. washwashed with THF
  3. customdried under vacuum

Sources & evidence

ORD record
ord-ecc601441dd642e49b7a4e5d4c00cf69
Source dataset
uspto-grants-2012_04
Patent number
US08158637B2

Reaction notes

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