H-Phe-Pro-OMe → H-Glu(Bzl)-Pro-OMe trifluoroacetate

HRID 622642Notes

Reaction equation

HRID 622642 reaction equation
[NH2:1][C@H:2]([C:10]([N:12]1[CH2:20][CH2:19][CH2:18][C@H:13]1[C:14]([O:16][CH3:17])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=CC=CC=1.N[C@H](C(N1CCC[C@H]1C(OC)=O)=O)CCCCNC([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=O.[F:49][C:50]([C:53]([OH:55])=[O:54])([F:52])[F:51]>>[NH2:1][C@H:2]([C:10]([N:12]1[CH2:20][CH2:19][CH2:18][C@H:13]1[C:14]([O:16][CH3:17])=[O:15])=[O:11])[CH2:3][CH2:4][C:9](=[O:54])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[F:49][C:50]([C:53]([OH:55])=[O:54])([F:52])[F:51]

Participants

3

Reactant 2

HCID 11311926H-Phe-Pro-OMeHCID 131667640Methyl N6-((benzyloxy)carbonyl)-L-lysyl-L-prolinate, 2,2,2-trifluoroacetate salt2×

Product 1

HCID 131715717H-Glu(Bzl)-Pro-OMe trifluoroacetate

Procedure

Instead of H-Phe-Pro-OMe (1 equivalent) and TEA (1 equivalent) in (b), (c) H-Lys(Z)-Pro-OMe trifluoroacetate (1 equivalent) and TEA (2 equivalents) were used to obtain (c') oleoyl-Lys(Z)-Pro-OMe (SUAM 1197) as an oil, and (d) H-Glu(Bzl)-Pro-OMe trifluoroacetate (1 equivalent) and TEA (2-equivalents) were used to obtain (d') oleoyl-Glu(Bzl)-Pro-OMe (SUAM 1196) as an oil.

Sources & evidence

ORD record
ord-3785bccf6be04a3d96a19d4c5a08f59e
Source dataset
uspto-grants-1988_09
Patent number
US04772587

Reaction notes

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