Hydrochloric Acid → (R)-Methyl 4-(cyclopropylsulfonyl)-3-(pyrrolidin-2-yl)phenylcarbamate hydrochloride

HRID 1515553Notes

Reaction equation

HRID 1515553 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH3:17])=[O:15])=[CH:9][C:8]=2[C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2C(OC(C)(C)C)=O)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[ClH:30].O1CCOCC1>CCOC(C)=O>[ClH:30].[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:15])[O:16][CH3:17])=[CH:9][C:8]=2[C@H:18]2[CH2:22][CH2:21][CH2:20][NH:19]2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59191692HCID 59191692, compound

Product 1

HCID 86645212(R)-Methyl 4-(cyclopropylsulfonyl)-3-(pyrrolidin-2-yl)phenylcarbamate hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 85I (1.63 g, 3.84 mmol) in EtOAc (15.0 mL) at rt was added 4.0 N HCl in dioxane (30 mL, 120 mmol). The mixture was stirred at rt for 4.0 h. TLC and LC-MS indicated a clean formation of the product. After evaporation of solvent, 85J (1.31 g, 95% yield) was obtained as a white solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 0.98-1.10 (m, 3H) 1.21-1.33 (m, 1H) 2.10-2.20 (m, 1H) 2.24-2.34 (m, 2 H) 2.41-2.50 (m, 1H) 2.80-2.89 (m, 1H) 3.31-3.41 (m, 2H) 3.70 (s, 3H) 5.45 (t, J=7.69 Hz, 1H) 7.54 (dd, J=8.79, 2.20 Hz, 1H) 7.85 (d, J=8.79 Hz, 1H) 7.99 (d, J=2.20 Hz, 1H), LC-MS 325 (M+H).

Workup

  1. customAfter evaporation of solvent

Sources & evidence

ORD record
ord-6e50f3a9a1e149eeb14c9ac469204c65
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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