HCID 67704936, compound → HCID 22876449, compound

HRID 1376690Notes

Reaction equation

HRID 1376690 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2([CH2:22][C:23]([NH:25][CH2:26][C:27]([NH:29][C@H:30]([C:35]([NH:37][C@H:38]([C:46]([OH:48])=[O:47])[CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:36])[CH2:31][C:32](=[O:34])[OH:33])=[O:28])=[O:24])OCC[O:18]2)=[CH:13][CH:12]=1)(=[NH:10])[NH2:9]>FC(F)(F)C(O)=O.O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH2:22][C:23]([NH:25][CH2:26][C:27]([NH:29][C@H:30]([C:35]([NH:37][C@H:38]([C:46]([OH:48])=[O:47])[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:36])[CH2:31][C:32](=[O:33])[OH:34])=[O:28])=[O:24])=[O:18])=[CH:13][CH:12]=1)(=[NH:9])[NH2:10]

Participants

3

Reactant 1

HCID 67704936HCID 67704936, compound

Product 1

HCID 22876449HCID 22876449, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

A solution of 100 mg of N-[N-[N-[[2-(p-amidinophenyl)-1,3-dioxolan-2-yl]acetyl]glycyl]-L-α-aspartyl]-3-phenyl-L-alanine trifluoroacetate in 10 ml of trifluoroacetic acid/water 9:1 is left to stand at room temperature overnight. After removal of the solvent, chromatography of the residue (RP-18; elution with water-water/acetonitrile 1:1) and recrystallization there are obtained 33 mg of N-[N-[N-[(p-amidinobenzoyl)acetyl]glycyl]-L-aspartyl]-3-phenyl-L-alanine trifluoroacetate (1:1), m.p. 225°-230° C. (decomposition).

Workup

  1. customAfter removal of the solvent, chromatography of the residue (RP-18; elution with water-water/acetonitrile 1:1) and recrystallization there

Sources & evidence

ORD record
ord-c388469379b84a8a84b2e4bf415b81e1
Source dataset
uspto-grants-1997_09
Patent number
US05663297

Reaction notes

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