Aminoacetonitrile hydrochloride → Tert-butyl 4-{4-[(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)(phenyl)methyl]benzoyl}piperazine-1-carboxylate

HRID 1180380Notes

Reaction equation

[K+].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:24][CH:25]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:26]([O-])=[O:27])=[CH:19][CH:18]=2)=[O:16])[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].Cl.[NH2:40][CH2:41][C:42]#[N:43]>>[C:42]([CH2:41][NH:40][C:26]([CH:25]([O:24][CH:23]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:20]1[CH:19]=[CH:18][C:17]([C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:7]([O:6][C:2]([CH3:3])([CH3:4])[CH3:5])=[O:8])[CH2:14][CH2:13]2)=[O:16])=[CH:22][CH:21]=1)[CH2:29][CH:30]([CH3:32])[CH3:31])=[O:27])#[N:43]

Participants

Reactant 2

HCID 11491918Aminoacetonitrile hydrochloride

HCID 694738852-[(4-{[4-(Tert-butoxycarbonyl)piperazin-1-yl]carbonyl}phenyl)(phenyl)methoxy]-4-methylpentanoic acid potassium salt

Product 1

HCID 86605379Tert-butyl 4-{4-[(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)(phenyl)methyl]benzoyl}piperazine-1-carboxylate

Procedure

Using the same procedure as described in step 3, 2-[(4-{[4-(tert-butoxycarbonyl)piperazin-1-yl]carbonyl}phenyl)(phenyl)methoxy]-4-methylpentanoic acid potassium salt from step 4 (0.55 g, 1.1 mmol) was coupled with amino acetonitrile HCl salt. The crude product was chromatographed on silica gel using 5% methanol in dichloromethane to afford the title compound as a white solid.

Workup

customThe crude product was chromatographed on silica gel using 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-da77d22df8d447e8894bc724a4c46e34
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279478B2

Reaction notes

Loading…