Triethylamine → 1-[(2S,3S)-3-(N2-t-Butoxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide

HRID 1780245Notes

Reaction equation

HRID 1780245 reaction equation
N#N.[C:3]([O:7][C:8]([NH:10][C@H:11]([C:16]([OH:18])=O)[CH2:12][C:13](=[O:15])[NH2:14])=[O:9])([CH3:6])([CH3:5])[CH3:4].C(N(CC)CC)C.[NH2:26][C@@H:27]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C@H:28]([OH:43])[C:29]([N:31]1[CH2:42][CH2:41][CH2:40][C@H:32]1[C:33]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:30]>CN(C)C=O>[C:3]([O:7][C:8]([NH:10][C@H:11]([C:16]([NH:26][C@@H:27]([CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C@H:28]([OH:43])[C:29]([N:31]1[CH2:42][CH2:41][CH2:40][C@H:32]1[C:33]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:30])=[O:18])[CH2:12][C:13](=[O:15])[NH2:14])=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99750051-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamideHCID 86750818N2 t-butoxycarbonyl-L-asparagine

Product 1

HCID 105549081-[(2S,3S)-3-(N2-t-Butoxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.5 g (43.9 mmol) of the p-nitrophenyl ester of N2 -t-butoxycarbonyl-L-asparagine and 7.33 g (72.3 mmol) of triethylamine were added, whilst ice-cooling, to a solution of 12.7 g (36.6 mmol) of 1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide [prepared as described in step (c) above] in 100 ml of dimethylformamide, and the mixture was stirred overnight at room temperature. At the end of this time, the reaction mixture was poured into ice-water, after which it was extracted with methylene chloride. The organic extract was then washed with a 1N aqueous solution of sodium hydroxide, with a 10% w/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride, in that order. The extract was then dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was recrystallized from a mixture of methylene chloride and hexane, to give 17.6 g of the title compound as a colorless powder, melting at 113°-115° C.

Workup

  1. extractionafter which it was extracted with methylene chloride
  2. extractionThe organic extract
  3. washwas then washed with a 1N aqueous solution of sodium hydroxide, with a 10% w/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialThe extract was then dried over anhydrous sodium sulfate
  5. customafter which the solvent was removed by distillation under reduced pressure
  6. customThe residue was recrystallized from a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-bb63b254fe3548599973473d042953d1
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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