Tributylphosphine → HCID 90418176, compound

HRID 2177185Notes

Reaction equation

HRID 2177185 reaction equation
[F:1][C:2]1([F:18])[CH2:6][CH2:5][CH:4]([C:7]2[C:11]([CH2:12][OH:13])=[C:10]([C:14]([F:17])([F:16])[F:15])[S:9][N:8]=2)[CH2:3]1.O[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:22]([CH3:33])[C:21]=1[CH3:34].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.P(CCCC)(CCCC)CCCC>>[F:18][C:2]1([F:1])[CH2:6][CH2:5][CH:4]([C:7]2[C:11]([CH2:12][O:13][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:22]([CH3:33])[C:21]=3[CH3:34])=[C:10]([C:14]([F:16])([F:17])[F:15])[S:9][N:8]=2)[CH2:3]1

Participants

5

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90418236HCID 90418236, compound

Product 1

HCID 90418176HCID 90418176, compound

Conditions

Temperature
60 °C

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed [3-(3,3-difluorocyclopentyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol (50 mg, 0.17 mmol, 1.00 equiv), tol (3 mL), ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate (77 mg, 0.35 mmol, 1.99 equiv), ADDP (87 mg, 0.35 mmol, 2.00 equiv), n-Bu3P (70 mg, 0.35 mmol, 1.99 equiv). The resulting solution was stirred for overnight at 60° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a TLC plate with ethyl acetate/petroleum ether (1/5). This resulted in 50 mg (crude) of ethyl 3-(4-[[3-(3,3-difluorocyclopentyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-2,3-dimethylphenyl)propanoate as yellow oil.

Workup

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 50 mg (crude) of ethyl 3-(4-[[3-(3,3-difluorocyclopentyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-2,3-dimethylphenyl)propanoate as yellow oil

Sources & evidence

ORD record
ord-a903a33d7c034ba1aa1065aa377f8df6
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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