1-Amidino-4-piperidinepropionic acid → Diisopropyl Ether

HRID 1376692Notes

Reaction equation

HRID 1376692 reaction equation
C(N1CCC(CCC(O)=O)CC1)(=N)N.NCC(N[C@H](C([NH:31][C@H:32]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=O)CC(=O)[O:23][C:24](C)([CH3:26])[CH3:25])=O.Cl.[NH+]1[CH:53]=[CH:52][CH:51]=CC=1>>[C:43]([O:42][C:40](=[O:41])[C@H:32]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH2:31])([CH3:46])([CH3:44])[CH3:45].[CH:24]([O:23][CH:52]([CH3:51])[CH3:53])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 155835111-Amidino-4-piperidinepropionic acidHCID 15674432H-Gly-Asp(OtBu)-Phe-OtBuHCID 21584435Pyridinium hydrochloride

Product 2

HCID 7914Diisopropyl EtherHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoate

Procedure

Analogously to Example 1B)e), by coupling 1.6 g of 1-amidino-4-piperidinepropionic acid with 1.8 g of H-Gly-Asp(OtBu)-Phe-OtBu in the presence of 928 mg of pyridinium hydrochloride there are obtained 2.1 g of N-[N-[N-[3-(1-amidino-4-piperidinyl)propionyl]glycyl]-3-t-butoxycarbonyl)-L-alanyl]-3-phenyl-L-alanine t-butyl ester, m.p. 104°-106° C. (diisopropyl ether; decomposition).

Sources & evidence

ORD record
ord-3774f3a1752b406797ab741a31ce7336
Source dataset
uspto-grants-1997_09
Patent number
US05663297

Reaction notes

Loading…