Trifluoroacetic acid → 2-Amino-3-[7-(6,7-difluoroquinolin-2-ylmethoxy)-11-methyl-10,11-dihydro-5h-benzo[e]pyrido[2,3-b]azepin-5-ylsulfanyl]-propionic acid ethyl ester

HRID 226268Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]3[CH2:24][N:23]([CH3:25])[C:22]4[N:26]=[CH:27][CH:28]=[CH:29][C:21]=4[CH:20](O)[C:19]=3[CH:31]=1)[CH:6]=[CH:5]2.Cl.[CH2:33]([O:35][C:36](=[O:41])[C@H:37]([CH2:39][SH:40])[NH2:38])[CH3:34].FC(F)(F)C(O)=O>ClCCl>[CH2:33]([O:35][C:36](=[O:41])[CH:37]([NH2:38])[CH2:39][S:40][CH:20]1[C:19]2[CH:31]=[C:15]([O:14][CH2:13][C:7]3[CH:6]=[CH:5][C:4]4[C:9](=[CH:10][C:11]([F:12])=[C:2]([F:1])[CH:3]=4)[N:8]=3)[CH:16]=[CH:17][C:18]=2[CH2:24][N:23]([CH3:25])[C:22]2[N:26]=[CH:27][CH:28]=[CH:29][C:21]1=2)[CH3:34]

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 6.6 g (15.7 mmol) of the product from Example 21, step 5, 6.0 g (32.3 mmol) of L-cystein ethyl ester hydrochloride and 136 ml of trifluoroacetic acid in 198 ml of dichloromethane is stirred at 45° C. for 16 hr. The solvent is evaporated and the residue partitioned between sat. NaHCO3 and chloroform. The organic layer is washed with water, dried and concentrated, giving an oil, which solidifies with the aid of diisopropyl ether/petroleum ether. Yield 7.9 g (91%).

Workup

customThe solvent is evaporated
customthe residue partitioned between sat. NaHCO3 and chloroform
washThe organic layer is washed with water
customdried
concentrationconcentrated
customgiving an oil, which

Sources & evidence

ORD record: ord-8cc0dd3b505743228175aba868c2d379
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557212B2

Reaction notes

Loading…