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

HRID 2293382Notes

Reaction equation

HRID 2293382 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.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:37]([NH:44][C:45](=[O:51])[C@H:46]([CH:48]([CH3:50])[CH3:49])[NH2:47])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1>[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:44]([CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:45](=[O:51])[C@H:46]([CH:48]([CH3:50])[CH3:49])[NH2:47])=[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

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 11063601(2S)-2-Amino-N-benzyl-3-methylbutanamideHCID 542297011-(2-adamantan-1-yl-2-oxoethyl) L-proline

Product 1

HCID 67634856L-valine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamideYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 3, a solution of 1-(2-adamantan-1-yl-2-oxoethyl) L-proline (109.1 mg, 0.37 mmol, 1.0 eq), triethylamine (156 uL, 1.12 mmol, 3.0 eq), and THF (1.5 mL), was treated with isobutyl chloroformate (53 uL, 0.41 mL, 1.1 eq), then with L-valine benzylamide (117.5 mg, 570 umol, 1.5 eq). Workup as before provided 127 mg (71%) of L-valine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide as a white foam.

Sources & evidence

ORD record
ord-e5cd1097e4f44fa2a3dfc1165ce7f1b9
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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