Thionyl Chloride → HCID 58003814, compound

HRID 1803470Notes

Reaction equation

S(Cl)(Cl)=O.[NH2:5][C@@:6]1([C:26]([OH:28])=[O:27])[C@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:10][C@@H:9]2[C@H:7]1[C@@:8]2([F:25])[C:22]([OH:24])=[O:23].[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]O)=[CH:32][CH:31]=1>>[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][O:23][C:22]([C@:8]2([F:25])[C@@H:7]3[C@H:9]2[CH2:10][C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[C@@:6]3([NH2:5])[C:26]([OH:28])=[O:27])=[O:24])=[CH:32][CH:31]=1

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 680224-Fluorobenzylic alcohol

HCID 9886034MGS-0039

Product 1

HCID 58003814HCID 58003814, compound

Conditions

Temperature: 60 °C

Procedure

23 μL of thionyl chloride was added to 30 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid suspended in 0.3 mL of 4-fluorobenzyl alcohol at room temperature, and the mixture was stirred for 3 days at 60° C. After standing to cool, the reaction solution was purified by reverse phase chromatography (Wako gel 50C18 (made by Wako Pure Chemical Industries Ltd.) eluent: water, a 70% aqueous solution of acetonitrile), thereby yielding 5 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-(4-fluorobenzyl)ester.

Workup

temperatureto cool
customthe reaction solution was purified by reverse phase chromatography (Wako gel 50C18 (made by Wako Pure Chemical Industries Ltd.) eluent

Sources & evidence

ORD record: ord-09338e25932042c384c49887a6474e13
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08350060B2

Reaction notes

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