Acetate → Lamifiban

HRID 1077917Notes

Reaction equation

HRID 1077917 reaction equation
C([O-])(=O)C.[C:5]([C:8]1[CH:46]=[CH:45][C:11]([C:12]([NH:14][C@H:15]([C:28]([N:30]2[CH2:35][CH2:34][CH:33]([O:36][CH2:37][C:38]([O:40]C(C)(C)C)=[O:39])[CH2:32][CH2:31]2)=[O:29])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]C(C)(C)C)=[CH:19][CH:18]=2)=[O:13])=[CH:10][CH:9]=1)(=[NH:7])[NH2:6].FC(F)(F)C([O-])=O>O.CO>[C:5]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][C@H:15]([C:28]([N:30]2[CH2:35][CH2:34][CH:33]([O:36][CH2:37][C:38]([OH:40])=[O:39])[CH2:32][CH2:31]2)=[O:29])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)=[O:13])=[CH:45][CH:46]=1)(=[NH:6])[NH2:7]

Participants

5

Reactant 3

HCID 175AcetateHCID 84468TrifluoroacetateHCID 10257638HCID 10257638, compound

Product 1

HCID 3038484Lamifiban

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

From 2.5 g of the acetate of t-butyl [[1-[N-(p-amidinobenzoyl)-3-(p-t-butoxyphenyl)-L-alanyl]-4-piperidinyl]oxy]-acetate there is obtained in analogy to Example 1, after chromatography (silylated silica get RP-18, water/methanol gradient), 1.0 g of [[1-[N-(p-amidinobenzoyl)-L-tyrosyl]-4-piperidinyl]oxy]acetic acid as the trifluoroacetate. M.p. 125°-130° C. (ethyl acetate, decomposition). MS (FAB): 469 (M+H)+.

Sources & evidence

ORD record
ord-0ffcbfaf16f7431ea671799714f736db
Source dataset
uspto-grants-1996_08
Patent number
US05545658

Reaction notes

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