4-Methylmorpholine → N-(3-Phenylpropionyl)-L-prolyl-L-proline benzyl ester

HRID 1720490Notes

Reaction equation

Cl.[CH2:2]([O:9][C:10](=[O:16])[C@@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN1CCOCC1.[C:24]1([CH2:30][CH2:31][C:32]([N:34]2[CH2:41][CH2:40][CH2:39][C@H:35]2[C:36](O)=[O:37])=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH2:2]([O:9][C:10](=[O:16])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:36](=[O:37])[C@@H:35]1[CH2:39][CH2:40][CH2:41][N:34]1[C:32](=[O:33])[CH2:31][CH2:30][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: -25 °C

Procedure

To L-proline benzyl ester hydrochloride (0.98 g) in dichloromethane (20 ml) were added N-methylmorpholine (0.49 ml), N-(3-phenylpropionyl)-L-proline (1.00 g) and HOBt (0.60 g) under ice-cooling. After cooling to -25° C. , DCC (0.92 g) was added, and the mixture was stirred at a temperature between -25° C. and 0° C. for 2 hours, and then at room temperature for 14 hours. The reaction mixture was treated and purified as in Example 7-A) to give 1.39 g of the title compound.

Workup

temperaturecooling
waitat room temperature for 14 hours
additionThe reaction mixture was treated
custompurified as in Example 7-A)

Sources & evidence

ORD record: ord-ca8de61c60974b23bf640984089acfec
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506256

Reaction notes

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