Methyl iodide → HCID 86654482, compound

HRID 1952430Notes

Reaction equation

HRID 1952430 reaction equation
[C:1](N1C[C@@H](S)[C@H](N(C)S(C2C=CC(OC3C=CC=CC=3)=CC=2)(=O)=O)C1)(=O)N.[C:28]([N:35]1[CH2:39][C@@H:38]([S:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C@H:37]([NH:45][S:46]([C:49]2[CH:54]=[CH:53][C:52]([O:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)=[CH:51][CH:50]=2)(=[O:48])=[O:47])[CH2:36]1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C(O[K])(C)(C)C.CI>CN(C=O)C.C(OCC)(=O)C>[C:28]([N:35]1[CH2:39][C@@H:38]([S:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C@H:37]([N:45]([CH3:1])[S:46]([C:49]2[CH:50]=[CH:51][C:52]([O:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)=[CH:53][CH:54]=2)(=[O:47])=[O:48])[CH2:36]1)([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 86654479HCID 86654479, compoundHCID 86654483HCID 86654483, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 86654482HCID 86654482, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(±)-N-Carbamoyl-trans-3-(N-methyl-4-phenoxybenzenesulfonamido)-4-mercaptopyrrolidine. To a solution of (±)-N-Boc-trans-3-(4-phenoxybenzenesulfonamido)-4-tert-butylmercaptopyrrolidine (236 mg, 0.466 mmol) in DMF (2 mL) at 0° C. was added tBuOK (0.69 mmol). The mixture was stirred at 0° C. for 10 min, then MeI (0.69 mmol) was added. The solution was stirred at 0° C. until TLC analysis showed no starting material remained. Ethyl acetate (20 mL) was added and the solution was extracted with water, then was dried over Na2SO4 and filtered. The solvent was evaporated and the residue was purified by flash chromatography (ethyl acetate) to give (±)-N-Boc-trans-3-(N-methyl-4-phenoxybenzenesulfonamido)-4-tertbutylmercaptopyrrolidine as a white powder (240 mg, 99%): 1H NMR (300 MHz, CD3OD) δ 7.84 (d, J=8, 2H), 7.44 (t, J=8, 2H), 7.24 (t, J=8, 1H), 7.10 (m, 2H), 7.09 (d, J=9, 2H), 4.22 (m, 1H), 3.90 (m, 1H), 3.37 (m, 2H), 3.08 (m, 2H) 2.86 (s, 3H), 1.44 (s, 9H), 1.28 (s, 9H); MS (ESI) m/e 520.2 (M+); HRMS (ESI) calculated for C26H36N2O5S2Na+ 543.1950. found 543.1950.

Workup

  1. stirringThe solution was stirred at 0° C. until TLC analysis
  2. extractionthe solution was extracted with water
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customthe residue was purified by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-cce19271cdbe477a8763254d970487b2
Source dataset
uspto-grants-2013_03
Patent number
US08404866B2

Reaction notes

Loading…