Hydrochloric Acid → HCID 86654484, compound

HRID 1952431Notes

Reaction equation

HRID 1952431 reaction equation
Cl.[C:2]([N:9]1[CH2:13][C@@H:12]([S:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:11]([N:19]([CH3:36])[S:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:10]1)(OC(C)(C)C)=[O:3].C([N:39](CC)CC)C.[Si](N=C=O)(C)(C)C>C(OCC)(=O)C>[C:2]([N:9]1[CH2:13][C@@H:12]([S:14][C:15]([CH3:16])([CH3:18])[CH3:17])[C@H:11]([N:19]([CH3:36])[S:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)(=[O:21])=[O:22])[CH2:10]1)(=[O:3])[NH2:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 86654482HCID 86654482, compound

Product 1

HCID 86654484HCID 86654484, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1.5 M HCl in ethyl acetate (5 mL) was added (±)-N-Boc-trans-3-(N-methyl-4-phenoxybenzenesulfonamido)-4-tertbutylmercaptopyrrolidine (130 mg, 0.25 mmol) and stirring was continued at room temperature until no starting material was detected by TLC. The solvent was evaporated under reduced pressure and the residue was dissolved in CH2Cl2. The solution was cooled to 0° C. and triethylamine (46 μL, 0.33 mmol) and TMSNCO (100 μL, 0.74 mmol) were added successively. The solution was stirred at room temperature overnight. The reaction mixture was extracted with water and saturated brine, and was dried over Na2SO4 and filtered. The solvent was evaporated and the residue was purified by flash chromatography (5% MeOH in ethyl acetate) to give (±)-N-carbamoyl-trans-3-(N-methyl-4-phenoxybenzenesulfonamido)-4-tert-butylmercaptopyrrolidine as a white powder (110 mg, 95%): 1H NMR (300 MHz, CD3OD) δ 7.85 (m, 2H), 7.42 (m, 2H), 7.22 (m, 1H), 7.10 (m, 4H), 4.24 (m, 1H), 3.96 (m, 1H), 3.42 (m, 2H), 3.08 (m, 2H), 2.87 (s, 3H), 1.28 (s, 9H); MS (ESI) m/e 463.2 (M+); HRMS (ESI) calcd for C22H29N3O4S2Na+ 486.1479. found 486.1481.

Workup

  1. customwas continued at room temperature until no starting material
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. stirringThe solution was stirred at room temperature overnight
  5. extractionThe reaction mixture was extracted with water and saturated brine
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. customThe solvent was evaporated
  9. customthe residue was purified by flash chromatography (5% MeOH in ethyl acetate)

Sources & evidence

ORD record
ord-3c0e91d8408940799edb4f82f0199900
Source dataset
uspto-grants-2013_03
Patent number
US08404866B2

Reaction notes

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