Hydrochloric Acid → (R)-Methyl (4-(isopropylsulfonyl)-3-(pyrrolidin-2-yl)phenyl)carbamate hydrochloride

HRID 1515499Notes

Reaction equation

HRID 1515499 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:20]([CH:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2C(OC(C)(C)C)=O)[CH:7]=1.[Cl:26][C:27]([O:29][CH3:30])=[O:28].Cl>N1C=CC=CC=1>[ClH:26].[CH:23]([S:20]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:27](=[O:28])[O:29][CH3:30])=[CH:7][C:6]=1[C@H:8]1[CH2:12][CH2:11][CH2:10][NH:9]1)(=[O:21])=[O:22])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 57942759(R)-tert-butyl 2-(5-amino-2-(isopropylsulfonyl)phenyl)pyrrolidine-1-carboxylate

Product 1

HCID 86645208(R)-Methyl (4-(isopropylsulfonyl)-3-(pyrrolidin-2-yl)phenyl)carbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1F (0.1 g, 0.27 mmol) in pyridine (1 mL) at 0° C. was added methyl chloroformate (57 (μL, 0.54 mmol). After 2.0 h of stirring at rt the reaction was acidified with 1M HCl to pH 3-4. The product was extracted with ethyl acetate and was washed with brine and dried over sodium sulfate. After evaporation of the solvent, the crude product was redissolved in ethyl acetate (1.5 mL) and hydrogen chloride (2 mL, 4M in dioxane) was added. The reaction was stirred for 3 h at rt. The solvent was removed and placed on the lyophilizer to give 0.15 g white solid 1G. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.25 (t, J=7.09 Hz, 3H) 1.37 (d, J=6.85 Hz, 3 H) 2.13-2.31 (m, 1H) 2.31-2.47 (m, 2H) 2.47-2.63 (m, 1H) 3.36-3.56 (m, 3H) 3.73-3.91 (m, 3H) 5.43 (t, J=7.70 Hz, 1H) 7.66 (dd, J=8.80, 2.20 Hz, 1H) 7.97 (d, J=8.80 Hz, 1H) 8.11 (d, J=1.96 Hz, 1H).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washwas washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation of the solvent
  5. dissolutionthe crude product was redissolved in ethyl acetate (1.5 mL)
  6. additionhydrogen chloride (2 mL, 4M in dioxane) was added
  7. stirringThe reaction was stirred for 3 h at rt
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-49144a6ad06744cdb1bbfa8fc0fa9e9e
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

Loading…