Oleoyl chloride → palmitoyl-Leu-Pro-OMe

HRID 622641Notes

Reaction equation

HRID 622641 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]CC.[NH2:21][C@H:22]([C:38]([N:40]1[CH2:48][CH2:47][CH2:46][C@H:41]1[C:42]([O:44][CH3:45])=[O:43])=[O:39])[CH2:23][CH2:24][CH2:25]CNC(OCC1C=CC=CC=1)=O.F[C:50](C(O)=O)(F)F>N(C(OCC1C=CC=CC=1)=O)[C@H](C(O)=O)C(C)C.N[C@H](C(N[C@H](C(N1CCC[C@H]1C(OC)=O)=O)CC(C)C)=O)CC(C)C>[NH:21]([C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:19])[C@H:22]([C:38]([N:40]1[CH2:48][CH2:47][CH2:46][C@H:41]1[C:42]([O:44][CH3:45])=[O:43])=[O:39])[CH2:23][CH:24]([CH3:25])[CH3:50]

Participants

5

Reactant 2

HCID 5364783Oleoyl chlorideHCID 131667640Methyl N6-((benzyloxy)carbonyl)-L-lysyl-L-prolinate, 2,2,2-trifluoroacetate salt2×

Product 1

HCID 131715720palmitoyl-Leu-Pro-OMe

Reagents, catalysts & solvents 2

HCID 726987N-Carbobenzoxy-L-valineSolventHCID 131715721H-Leu-Leu-Pro-OMeSolvent

Procedure

Instead of oleoyl chloride in (b), (a) palmitoyl chloride, (b) stearoyl chloride and (c) linoleolyl chloride were used to obtain (a') palmitoyl-Leu-Pro-OMe (SUAM 1141), (b') stearoyl-Leu-Pro-OMe (SUAM 1142) and (c') linoleoyl-Leu-Pro-OMe (SUAM 1143), respectively. Further, instead of H-Leu-Pro-OMe in (b), (d) H-Val-Pro-OMe, (e) H-Ala-Pro-OMe (f) H-Leu-Leu-Pro-OMe, (g) H-Phe-Pro-OMe, (h) H-Met-Pro-OMe and (i) H-norLeu-Pro-OMe were used to obtain (d') oleoyl-Val-Pro-OMe (SUAM 1147), (e') oleoyl -Ala-Pro-OMe (SUAM 1076), (f') oleoyl-Leu-Leu-Pro-OMe (SUAM 1159), (g') oleoyl-Phe-Pro-OMe (SUAM) 1194), (h') oleoyl-Met-Pro-OMe (SUAM 1198) and (i') oleoyl-norLeu-Pro-OMe (SUAM 1164), as oils, respectively.

Sources & evidence

ORD record
ord-769ae782d43b448698f48b4977beb9eb
Source dataset
uspto-grants-1988_09
Patent number
US04772587

Reaction notes

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