HCID 131716517, compound → HCID 131716516, compound

HRID 1709961Notes

Reaction equation

HRID 1709961 reaction equation
[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22](O)=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:32][C@H:33]([C:39]([NH:41][C:42]1[CH:51]=[C:50]2[C:45]([C:46]([CH3:53])=[CH:47][C:48](=[O:52])[O:49]2)=[CH:44][CH:43]=1)=[O:40])[CH2:34][CH2:35][C:36](=[O:38])[NH2:37].FC(C(O)=O)(F)F>>[NH:1]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([NH:32][C@H:33]([C:39]([NH:41][C:42]1[CH:51]=[C:50]2[C:45]([C:46]([CH3:53])=[CH:47][C:48](=[O:52])[O:49]2)=[CH:44][CH:43]=1)=[O:40])[CH2:34][CH2:35][C:36](=[O:38])[NH2:37])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 131716517HCID 131716517, compoundHCID 131716518HCID 131716518, compound

Product 1

HCID 131716516HCID 131716516, compound

Procedure

Boc-Phe-Gly-Leu-Gln-AMC was prepared by coupling Boc-Phe-Gly-Leu-OH (0.39 g, 0.90 mmol) to H-Gln-AMC trifluoroacetate (0.41 g, 0.99 mmol) by a mixed anhydride coupling procedure to yield 0.49 g crude product. Product was recrystallized from ethyl acetate to provide 0.27 g of Boc-Phe-Gly-Leu-Gln-AMC, mp 234°-236° with decomposition. TLC with methanol:chloroform (1:9) showed a single spot, Rf 0.20.

Workup

  1. customto yield 0.49 g crude product

Sources & evidence

ORD record
ord-42663569da8e4c8488a8a3019eda363b
Source dataset
uspto-grants-1990_08
Patent number
US04952493

Reaction notes

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