Triethylamine → HCID 131720283, compound

HRID 2293392Notes

Reaction equation

HRID 2293392 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.[CH3:22][O:23][C:24]1[CH:39]=[CH:38][CH:37]=[CH:36][C:25]=1[CH2:26][NH:27][C:28](=[O:35])[C@H:29]([C@H:31]([CH2:33][CH3:34])[CH3:32])[NH2:30].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:27]([CH2:26][C:25]3[CH:36]=[CH:37][CH:38]=[CH:39][C:24]=3[O:23][CH3:22])[C:28](=[O:35])[C@H:29]([C@H:31]([CH2:33][CH3:34])[CH3:32])[NH2:30])=[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 42312965HCID 42312965, compoundHCID 542297011-(2-adamantan-1-yl-2-oxoethyl) L-proline

Product 1

HCID 131720283HCID 131720283, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Using the procedure described previously, a solution of 1-(2-adamantan-1-yl-2-oxoethyl) L-proline (179 mg, 0.61 mmol, 1.0 eq), L-isoleucine 2-methoxybenzylamide (308 mg, 1.23 mmol) and dichloromethane (2 mL), was treated with triethylamine (515 uL, 6.0 eq), and a 50% solution of 1-n-propylphosphonic acid cyclic anhydride in dichloromethane (783 uL, 2.0 eq), to provide 254 mg (79%) of L-isoleucine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] 2-methoxybenzylamide.

Sources & evidence

ORD record
ord-42c863411f7b4426adb8eeb387505302
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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