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

HRID 2293387Notes

Reaction equation

HRID 2293387 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](O)=[O:16])[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:37])[C@H:31]([CH2:33][C:34](=[O:36])[NH2:35])[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:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:30](=[O:37])[C@H:31]([CH2:33][C:34](=[O:36])[NH2:35])[NH2:32])=[O:16])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 54193114L-asparagine N-benzylamideHCID 542297011-(2-adamantan-1-yl-2-oxoethyl) L-proline

Product 1

HCID 67620109L-asparagine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Using the procedure described previously, a heterogeneous solution of 1-(2-adamantan-1-yl-2-oxoethyl) L-proline (152 mg, 0.52 mmol, 1.0 eq), L-asparagine N-benzylamide (231 mg, 1.04 mmol, 2.0 eq) and dichloromethane (1.5 mL), was treated with triethylamine (436 uL, 3.1 mmol, 6.0 eq), and a 50% solution of 1-n-propylphosphonic acid cyclic anhydride in dichloromethane (663 uL, 1.04 mL, 2.0 eq), to provide 130.7 mg (51%) of L-asparagine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide as a white foam.

Sources & evidence

ORD record
ord-8906e862e259433a8406ede7487f99ed
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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