Triethylamine → HCID 15389022, compound

HRID 1735393Notes

Reaction equation

HRID 1735393 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH2:9]([N:16]=[C:17]=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:9]([NH:16][C:17]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76639Benzyl isocyanateHCID 145742L-Proline

Product 1

HCID 15389022HCID 15389022, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Proline (23.3 g), benzyl isocyanate (22.9 g) and triethylamine (20.5 g) were stirred at room temperature for 1 hour in DMF (250 ml) to give a solution of N-(benzylaminocarbonyl)-L-proline. Thereto were added HOBt (29.7 g), water-soluble carbodiimide hydrochloride (42.13 g), L-proline benzyl ester hydrochloride (48.3 g) and triethylamine (27.9 ml) under ice-cooling, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with 10% potassium hydrogensulfate, a saturated aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated to give the title compound (73.6 g).

Sources & evidence

ORD record
ord-9f315d97465b4983af0d0b7dd12e1d54
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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