Dichloromethane → HCID 86607061, compound

HRID 2253034Notes

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17](C=CC3C=NC=CC=3)[CH:16]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:29]CCl.[F:32][C:33]([F:46])([F:45])[S:34]([O:37]S(C(F)(F)F)(=O)=O)(=[O:36])=[O:35]>>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:37][S:34]([C:33]([F:46])([F:45])[F:32])(=[O:35])=[O:36])=[C:17]([Cl:29])[CH:16]=2)[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 67749Trifluoromethanesulfonic anhydride

HCID 67073511N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine2×

Product 1

HCID 86607061HCID 86607061, compoundYield 98%

Conditions

Temperature: 0 °C

Procedure

To the solution of 1.80 g (5.5 mmol) (R)-2-(3-chloro-4-hydroxy-benzyl)-morpholine-4-carboxylic acid tert-butyl ester (example 7, intermediate (a)) in 25 mL dichloromethane 1.53 mL (11.0 mmol) triethylamine were added. After cooling down to 0° C. 1.0 mL (6.0 mmol) trifluoromethanesulfonic anhydride were added and the cooling bath was removed. After 1 h stirring at room temperature the reaction mixture was extracted with 10% aqueous sodium bicarbonate solution and brine and the organic layer was dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel using n-hexane:ethyl acetate (2:1 v/v) as eluant to give the compound in form of a light yellow oil (98%).

Workup

customthe cooling bath was removed
extractionwas extracted with 10% aqueous sodium bicarbonate solution and brine
dry with materialthe organic layer was dried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-ce856bc8683445bd8c6907e780134932
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323466B2

Reaction notes

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