Ethyl cysteinate hydrochloride → 2-(R)-Amino-3-[7-(7-chloro-6-fluoro-quinolin-2-ylmethoxy)-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ylsulfanyl]-propionic acid ethyl ester

HRID 226267Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]=[C:7]([CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]3[CH2:28][CH2:27][C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[CH:20](O)[C:19]=3[CH:30]=1)[CH:6]=[CH:5]2.[ClH:31].[CH2:32]([O:34][C:35](=[O:40])[C@H:36]([CH2:38][SH:39])[NH2:37])[CH3:33]>FC(F)(F)C(O)=O>[CH2:32]([O:34][C:35](=[O:40])[C@@H:36]([NH2:37])[CH2:38][S:39][CH:20]1[C:21]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[CH2:27][CH2:28][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:7]3[CH:6]=[CH:5][C:4]4[C:9](=[CH:10][C:11]([Cl:31])=[C:2]([F:1])[CH:3]=4)[N:8]=3)=[CH:30][C:19]1=2)[CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 10.0 g (23.76 mmol) of the product from Example 23, step 7, 9.7 g (52.3 mmol) of L-cystein ethyl ester hydrochloride and 105 ml of trifluoroacetic acid is stirred at 60° C. for 48 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 is crystallised from ethyl ether/diisopropyl ether. Yield 10.4 g (80%).

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
customis crystallised from ethyl ether/diisopropyl ether

Sources & evidence

ORD record: ord-c0292cb7877c40b5a24dfefe1cef7f27
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557212B2

Reaction notes

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