Hydrochloric Acid → HCID 90015738, compound

HRID 920152Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:33])=[C:6]([C@:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])([CH3:20])[CH2:9][S:10][C:11]2([C:15]([O:17]CC)=[O:16])[CH2:14][CH2:13][CH2:12]2)[CH:7]=1.[OH-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:33])=[C:6]([C@:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])([CH3:20])[CH2:9][S:10][C:11]2([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12]2)[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (R)-ethyl 1-(2-(5-bromo-2-fluorophenyl)-2-(2,4-dimethoxybenzylamino)propylthio)cyclobutanecarboxylate (2 g, 3.7 mmol, Eq: 1.00) in ethanol (50 ml) was added 3 N NaOH (2.47 ml, 7.4 mmol, Eq: 2.0). The reaction solution was stirred at 70° C. for 2 hours. 1 N HCl (7.4 ml, 7.4 mmol, Eq: 2.0) was added to the reaction mixture at 23° C. (pH=5-6). After evaporation the residue was triturated with dichloromethane/methanol 9:1 and solid Na2SO4 was added. The solid was filtered off and the filtrate was evaporated to dryness to give the crude (R)-1-(2-(5-bromo-2-fluorophenyl)-2-(2,4-dimethoxybenzylamino)propylthio)cyclobutanecarboxylic acid (1.8 g, 3.51 mmol, 94.9% yield) as a white foam, which was used without further purification. MS (ISP): m/z=512.4 [M+H]+ and 514.4 [M+2+H]+.

Workup

customAfter evaporation the residue
customwas triturated with dichloromethane/methanol 9:1 and solid Na2SO4
additionwas added
filtrationThe solid was filtered off
customthe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-3292f409062b4cb580fb1e8892c4c0dc
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273042B2

Reaction notes

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