Triethylamine → HCID 131720281, compound

HRID 2293390Notes

Reaction equation

HRID 2293390 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.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][NH:29][C:30](=[O:37])[C@H:31]([C@H:33]([CH2:35][CH3:36])[CH3:34])[NH2:32].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:23]3[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=3)[C:30](=[O:37])[C@H:31]([C@H:33]([CH2:35][CH3:36])[CH3:34])[NH2:32])=[O:16])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13891223HCID 13891223, compoundHCID 542297011-(2-adamantan-1-yl-2-oxoethyl) L-proline

Product 1

HCID 131720281HCID 131720281, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Using the procedure described previously, a solution of 1-(2-adamantan-1-yl-2-oxoethyl) L-proline (165 mg, 0.56 mmol, 1.0 eq), L-isoleucine pyridin-2-ylmethylamide (246 mg, 1.11 mmol) and dichloromethane (2 mL), was treated with triethylamine (475 uL, 6.0 eq), and a 50% solution of 1-n-propylphosphonic acid cyclic anhydride in dichloromethane (721 uL, 2.0 eq), to provide 214 mg (77%) of L-isoleucine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] pyridin-2-ylmethylamide.

Sources & evidence

ORD record
ord-0a9236c8f17740d896c28daff7e793df
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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