Ammonia → trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-prolineamide

HRID 893166Notes

Reaction equation

HRID 893166 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:13]2[C:14](O)=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([N:25](CC)CC)C.ClC(OCC)=O.N>O1CCCC1>[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:13]2[C:14]([NH2:25])=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10566895trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Product 1

HCID 13455343trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-prolineamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.10 g of trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline and 1.10 g of triethylamine were dissolved in 40 ml of dried tetrahydrofuran, and a solution of 1.20 g of ethyl chloroformate in 10 ml of dried tetrahydrofuran was added dropwise thereto at -25° C. to -35° C. After stirring at the same temperature for 50 minutes, 10 ml of concentrated aqueous ammonia was added dropwise to the mixture at -25° to -40° C. The temperature was then gradually elevated to room temperature, and the reaction mixture was stirred for 1 hour, followed by concentration under reduced pressure To the residue were added 20 ml of water and 50 ml of diethyl ether. After ice-cooling, the thus formed white crystals were separated by filtration, washed successively with cool water and cool diethyl ether, and dried under reduced pressure to yield trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-prolineamide.

Workup

  1. customat -25° C. to -35° C
  2. customwas then gradually elevated to room temperature
  3. stirringthe reaction mixture was stirred for 1 hour
  4. concentrationfollowed by concentration under reduced pressure To the residue
  5. additionwere added 20 ml of water and 50 ml of diethyl ether
  6. temperatureAfter ice-cooling
  7. customthe thus formed white crystals were separated by filtration
  8. washwashed successively with cool water
  9. temperaturecool diethyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-9723341de699405a848f04781a77402d
Source dataset
uspto-grants-1992_06
Patent number
US05122604

Reaction notes

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