Triethylamine → N-[(Phenylmethoxy)carbonyl]-L-valyl-L-leucine methyl ester

HRID 1076408Notes

Reaction equation

[CH3:1][CH:2]([CH2:4][C@H:5]([NH2:10])[C:6]([O:8][CH3:9])=[O:7])[CH3:3].Cl.C(N(CC)CC)C.[NH:19]([C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[C@H:20]([C:24](O)=[O:25])[CH:21]([CH3:23])[CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[NH:19]([C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[C@H:20]([C:24]([NH:10][C@H:5]([C:6]([O:8][CH3:9])=[O:7])[CH2:4][CH:2]([CH3:3])[CH3:1])=[O:25])[CH:21]([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

19.9 g (110 mmols) of H-Leu-OMe. HCl are dissolved in 120 ml of dimethylformamide and 14.6 ml (105 mmols) of triethylamine are added at 0°C. The precipitated triethylamine hydrochloride is filtered off, the filtrate is added to a solution of 25.1 g (100 mmols) of Z-Val-OH in 200 ml of dimethylformamide (0°C), and 22.6 g (110 mmols) of dry dicyclohexylcarbodiimide are then added. After 1 hour's stirring at 0°C and standing overnight in the refrigerator the mixture is filtered and the solution evaporated in a high vacuum at 40°C. The oily residue is taken up in 30 ml of ethyl acetate, and the solution is cooled to 0°C and freed of precipitated dicyclohexylurea. After adding n-hexane the product crystallises out from the filtrate overnight. Melting point 102°-105°C; [α]D : -41° (c = 2.88 in methanol).

Workup

filtrationThe precipitated triethylamine hydrochloride is filtered off
additionare then added
waitstanding overnight in the refrigerator
filtrationthe mixture is filtered
customthe solution evaporated in a high vacuum at 40°C
temperaturethe solution is cooled to 0°C
additionAfter adding n-hexane the product
customcrystallises out from the filtrate overnight
custom-41° (c = 2.88 in methanol)

Sources & evidence

ORD record: ord-6b72145c00c5445480c08d3dec982508
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03956260

Reaction notes

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