Triethylamine → trans-1-(p-nitrobenzyloxycarbonyl)-4-methanesulfonyloxy-L-prolineamide

HRID 893167Notes

Reaction equation

HRID 893167 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N+:6]([C:9]1[CH:27]=[CH:26][C:12]([CH2:13][O:14][C:15]([N:17]2[CH2:24][C@H:23]([OH:25])[CH2:22][C@H:18]2[C:19]([NH2:21])=[O:20])=[O:16])=[CH:11][CH:10]=1)([O-:8])=[O:7].C(N(CC)CC)C>O1CCCC1>[N+:6]([C:9]1[CH:27]=[CH:26][C:12]([CH2:13][O:14][C:15]([N:17]2[CH2:24][C@H:23]([O:25][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:22][C@H:18]2[C:19]([NH2:21])=[O:20])=[O:16])=[CH:11][CH:10]=1)([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13455343trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-prolineamide

Product 1

HCID 13455346trans-1-(p-nitrobenzyloxycarbonyl)-4-methanesulfonyloxy-L-prolineamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.89 g of methanesulfonyl chloride in 10 ml of dried tetrahydrofuran was added dropwise to a suspension of 2.32 g of trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-prolineamide and 1.67 g of triethylamine in 40 ml of dried tetrahydrofuran at room temperature. After stirring for 1 hour, the reaction mixture was concentrated under reduced pressure, and to the residue were added 30 ml of water and 30 ml of diethyl ether. After cooling, the resulting white crystals were separated by filtration, washed successively with cool water and cool diethyl ether and dried under reduced pressure to obtain trans-1-(p-nitrobenzyloxycarbonyl)-4-methanesulfonyloxy-L-prolineamide.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionto the residue were added 30 ml of water and 30 ml of diethyl ether
  3. temperatureAfter cooling
  4. customthe resulting white crystals were separated by filtration
  5. washwashed successively with cool water
  6. temperaturecool diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-23db07f75b78437089e239744fe6e4d1
Source dataset
uspto-grants-1992_06
Patent number
US05122604

Reaction notes

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