Triethylamine → HCID 131720282, compound

HRID 2293391Notes

Reaction equation

HRID 2293391 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.[CH3:22][O:23][C:24]1[CH:39]=[CH:38][C:27]([CH2:28][NH:29][C:30](=[O:37])[C@H:31]([C@H:33]([CH2:35][CH3:36])[CH3:34])[NH2:32])=[CH:26][CH:25]=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]([CH2:28][C:27]3[CH:38]=[CH:39][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[C:30](=[O:37])[C@H:31]([C@H:33]([CH2:35][CH3:36])[CH3:34])[NH2:32])=[O:17])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 42312982HCID 42312982, compoundHCID 542297011-(2-adamantan-1-yl-2-oxoethyl) L-proline

Product 1

HCID 131720282HCID 131720282, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Using the procedure described previously, a solution of 1-(2-adamantan-1-yl-2-oxoethyl) L-proline (140 mg, 0.48 mmol, 1.0 eq), L-isoleucine 4-methoxybenzylamide (238 mg, 0.95 mmol) and dichloromethane (2 mL), was treated with triethylamine (400 uL, 6.0 eq), and a 50% solution of 1-n-propylphosphonic acid cyclic anhydride in dichloromethane (610 uL, 2.0 eq), to provide 207 mg (82%) of L-isoleucine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] 4-methoxybenzylamide.

Sources & evidence

ORD record
ord-3549b1fd408f4f9c8d5811d630397f89
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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