Tert-Butylamine → HCID 70051621, compound

HRID 1780273Notes

Reaction equation

HRID 1780273 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.[CH2:30]([O:37][C:38]([N:40]1[CH2:47][C@@H:46]([OH:48])[CH2:45][C@H:41]1[C:42](O)=[O:43])=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C=O>[CH2:30]([O:37][C:38]([N:40]1[CH2:47][C@@H:46]([OH:48])[CH2:45][C@H:41]1[C:42]([NH:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:43])=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 688414(2S,4S)-1-((Benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 70051621HCID 70051621, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.56 g (16.58 mmol) of diphenylphosphoryl azide, 1.50 g (20.55 mmol) of t-butylamine and 2.78 g (27.80 mmol) of triethylamine were successively added, whilst ice-cooling, to a solution of 3.68 g (13.90 mmol) of (4S)-1-benzyloxycarbonyl-4-hydroxy-L-proline in 30 ml of dimethylformamide, and the mixture was stirred for 5 hours. At the end of this time, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic extract was washed with a 10% w/v aqueous solution of citric acid, with a 10% w/v aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which the resulting mixture was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was recrystallized from a mixture of methylene chloride and diethyl ether, to give 1.10 g of the title compound as colorless crystals, melting at 129°-130° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with a 10% w/v aqueous solution of citric acid, with a 10% w/v aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialafter which the resulting mixture was dried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customthe residue was recrystallized from a mixture of methylene chloride and diethyl ether

Sources & evidence

ORD record
ord-990d51f506bc475787cc715f1ac2efc1
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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