Chloride → HCID 54058474, compound

HRID 2185456Notes

Reaction equation

HRID 2185456 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[O:13]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:41])[C@@H:28]2[CH2:32][C@H:31]([OH:33])[CH2:30][N:29]2[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-]>ClCCl.CN(C)C1C=CN=CC=1>[O:13]([C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:41])[C@@H:28]2[CH2:32][C@H:31]([O:33][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:30][N:29]2[C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 70176092HCID 70176092, compound

Product 1

HCID 54058474HCID 54058474, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (4.40 mL) and methanesulfonyl chloride (1.95 mL) was added to a cold (0° C.) stirred solution of cis-4-hydroxy-N-tert-butoxycarbonyl-L-proline 4-phenoxyphenylamide (C, 5.02 g) in dichloromethane (100 mL). The mixture was stirred at 0° C. for 2 hr and at room temperature for 45 min. Triethylamine (4.40 mL) and mehanesulfonyl chloride (1.95 mL) was added to the cold (0° C.) stirred mixture. The mixture was stirred at 0° C. to room temperature for 2 hr, and 4-dimethylaminopyridine (1.54 g) was added at 0° C. The mixture was stirred at room temperature for 1 hr and concentrated in vacuo. The residue was diluted with ethyl acetate and washed with 1 N hydrochloric acid, water, saturated sodium hydrogen carbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (6.49 g).

Workup

  1. stirringstirred mixture
  2. stirringThe mixture was stirred at 0° C. to room temperature for 2 hr
  3. stirringThe mixture was stirred at room temperature for 1 hr
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with 1 N hydrochloric acid, water, saturated sodium hydrogen carbonate, and brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8b62f7b700e4b4a955e221b0c17d398
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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