Triethylamine → HCID 21341440, compound

HRID 2185432Notes

Reaction equation

HRID 2185432 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH3:13][O:14][C:15](=[O:34])[C@@H:16]1[CH2:20][C@H:19]([OH:21])[CH2:18][N:17]1[C:22](=[O:33])[CH2:23][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:25]>ClCCl.C(Cl)(Cl)Cl>[CH3:13][O:14][C:15](=[O:34])[C@@H:16]1[CH2:20][C@H:19]([O:21][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:18][N:17]1[C:22](=[O:33])[CH2:23][N:24]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21341439HCID 21341439, compound

Product 1

HCID 21341440HCID 21341440, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (678 μL) and methanesulfonyl chloride (342 L) were added to a solution of 1-(N-tert-butoxycarbonyl-N-methylglycyl)-cis-4-hydroxy-L-proline methyl ester (A, 699 mg) in dichloromethane (15 mL) at 0° C. After stirring at 0° C. for 45 min and at room temperature for 45 min, the reaction mixture was diluted with chloroform. The organic layer was washed with 10% citric acid, saturated sodium hydrogen carbonate, and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to afford the title compound (0.82 g) as a pale yellow oil.

Workup

  1. washThe organic layer was washed with 10% citric acid, saturated sodium hydrogen carbonate, and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-0154c081a4ee480b9a5e29539f7ec81a
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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