L-Pyroglutamic Acid → HCID 14369414, compound

HRID 986353Notes

Reaction equation

HRID 986353 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=O.[C:10]1([CH2:16][CH2:17][NH:18][C:19](=[O:51])[C@H:20]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[NH:21][C:22](=[O:43])[C@H:23]([CH2:39][C:40](=[O:42])[NH2:41])[NH:24][C:25](=[O:38])[C@H:26]([CH2:36][OH:37])[NH:27][C:28](=[O:35])[CH2:29][NH:30][C:31](=[O:34])[CH2:32][NH2:33])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N=C=N>>[C:10]1([CH2:16][CH2:17][NH:18][C:19](=[O:51])[C@H:20]([CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:21][C:22](=[O:43])[C@H:23]([CH2:39][C:40](=[O:42])[NH2:41])[NH:24][C:25](=[O:38])[C@H:26]([CH2:36][OH:37])[NH:27][C:28](=[O:35])[CH2:29][NH:30][C:31](=[O:34])[CH2:32][NH:33][C:7](=[O:9])[C@@H:2]2[CH2:3][CH2:4][C:5](=[O:6])[NH:1]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 7405L-Pyroglutamic AcidHCID 160435CarbodiimideHCID 14369442HCID 14369442, compound

Product 1

HCID 14369414HCID 14369414, compoundYield 82%

Procedure

Pyroglutamyl-glycyl-glycyl-seryl-asparaginyl-phenylalanine 2-phenylethylamide is prepared from pyroglutamic acid and glycyl-glycyl-seryl-asparaginyl-phenylalanine 2-phenylethylamide using the carbodiimide method similar to that described in the preceding example 5. Yield 82 %, m.p. 209°-211° C., Rf 0.25/S1, 0.67/S2.

Sources & evidence

ORD record
ord-26c03ad87ab8456297fb509b9575e681
Source dataset
uspto-grants-1987_12
Patent number
US04711952

Reaction notes

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