Dichloromethane → HCID 118625621, compound

HRID 923817Notes

Reaction equation

HRID 923817 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[CH2:19]([C:21]1([CH2:25]O)[CH2:24][O:23][CH2:22]1)[CH3:20].ClCCl.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CCCCCCC.C(OCC)(=O)C>[CH2:19]([C:21]1([CH2:25][C:15]2[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=[CH:11][C:10]=2[C:4]2[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=2)[CH2:24][O:23][CH2:22]1)[CH3:20]

Participants

8

Reactant 4

HCID 6344Dichloromethane2×HCID 10868DicyclohexylcarbodiimideHCID 76444Oxt-101HCID 54595652HCID 54595652, compound

Product 1

HCID 118625621HCID 118625621, compoundYield 107.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

In step (c -2), 3′,4′,5′-trifluoro-[1,1′-biphenyl]-4-carboxylic acid (10.0 g, 37.0 mmol), 3-ethyl-3-hydroxymethyloxetane (5.9 g, 37 mmol), 4-dimethylaminopyridine (4.5 g, 37 mmol), and 100 ml of dichloromethane were mixed under nitrogen atmosphere and cooled to 0° C., and then 50 ml of a dichloromethane solution including 8.0 g (39 mmol) of dicyclohexylcarbodiimide was added dropwise thereto at 0° C., and the resulting mixture was stirred at room temperature for 15 hours. The mixture was filtrated by celite to collect a filtrate. The filtrate was condensed under a reduced pressure, followed by column chromatography (volume ratio of ethyl acetate:heptane=1:4) to obtain 13.9 g of (3-ethyloxetane-3-yl)methyl 3′,4′,5′-trifluoro-[1,1′-biphenyl]-4-carboxylic acid.

Workup

  1. additionwas added dropwise
  2. filtrationThe mixture was filtrated by celite
  3. customto collect a filtrate
  4. customcondensed under a reduced pressure

Sources & evidence

ORD record
ord-68b8dea0e28a491eb0e237ad6b42e9e7
Source dataset
uspto-grants-2016_03
Patent number
US09279083B2

Reaction notes

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