Trifluoroacetate → N-[N'-[3-(1-Piperazinyl)benzoyl]glycyl]-3(S)-ethynyl-beta-alanine trifluoroacetic acid salt

HRID 618164Notes

Reaction equation

HRID 618164 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=2)[C:17]([NH:19][CH2:20][C:21]([OH:23])=O)=[O:18])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C([O:30][C:31](=[O:37])[CH2:32][C@@H:33]([C:35]#[CH:36])[NH2:34])C.[F:38][C:39]([F:44])([F:43])[C:40]([O-:42])=[O:41]>>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[N:11]1([C:14]2[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=2)[C:17]([NH:19][CH2:20][C:21]([NH:34][C@H:33]([C:35]#[CH:36])[CH2:32][C:31]([OH:37])=[O:30])=[O:23])=[O:18])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 541317443-(4-t-Butoxycarbonyl-1-piperazinyl)benzoyl glycineHCID 86751219Ethyl (3s)-3-aminopent-4-ynoate hydrochloride

Product 1

HCID 86754488N-[N'-[3-(1-Piperazinyl)benzoyl]glycyl]-3(S)-ethynyl-beta-alanine trifluoroacetic acid salt

Procedure

The acid 17-1 was coupled with 3(S)-ethynyl-β-alanine ethyl ester hydrochloride (Zablocki et al., J. Med. Chem., 1995, 38, 2378-2394) using standard peptide coupling conditions. The product was then fully deprotected using previously described methodology to give, after reverse phase chromatography, 17-4 as the trifluoroacetate salt.

Workup

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Sources & evidence

ORD record
ord-96fba85a7bfe49e9a10bcfac5281a527
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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