Triethylamine → L-phenylalanine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide

HRID 2293384Notes

Reaction equation

[C:1]12([C:11](=[O:21])[CH2:12][N:13]3[CH2:20][CH2:19][CH2:18][C@H:14]3[C:15]([OH:17])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:22]([NH:29][C:30](=[O:40])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl>[C:1]12([C:11](=[O:21])[CH2:12][N:13]3[CH2:20][CH2:19][CH2:18][C@H:14]3[C:15]([N:29]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:30](=[O:40])[C@H:31]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[NH2:32])=[O:17])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

Conditions

Temperature: 22 °C

Procedure

Using the procedure described previously, a solution of 1-(2-adamantan-1-yl-2-oxoethyl) L-proline (100 mg, 0.34 mmol, 1.0 eq), L-phenylalanine N-benzylamide (175 mg, 686 umol, 2.0 eq) and dichloromethane (1.0 mL), was cooled to 0° C., and treated with triethylamine (286 uL, 2.0 mmol, 6.0 eq). To this chilled solution was added a 50% solution of 1-n-propylphosphonic acid cyclic anhydride in dichloromethane (436 uL, 0.68 mL, 2.0 eq). When TLC indicated the reaction was complete, the solution was allowed to warm to 22° C., washed with satd aq NaHCO3, concentrated in vacuo, and purified by flash chromatography to provide 144 mg (80%) of L-phenylalanine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide.

Workup

washwashed with satd aq NaHCO3
concentrationconcentrated in vacuo
custompurified by flash chromatography

Sources & evidence

ORD record: ord-d3c7d422d58641d7ae7e946754ee7b83
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686424

Reaction notes

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