HCID 66619734, compound → HCID 59402678, compound

HRID 415607Notes

Reaction equation

HRID 415607 reaction equation
[NH2:1][C:2]([C:4]1[C:5]([F:18])=[C:6]([CH:14]=[CH:15][C:16]=1[F:17])[O:7][CH2:8][CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[O:3]>C(O)CCC.[Rh]>[NH2:1][C:2]([C:4]1[C:5]([F:18])=[C:6]([CH:14]=[CH:15][C:16]=1[F:17])[O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:2][CH2:4][CH2:16][CH3:15])=[O:12])=[O:3]

Participants

4

Reactant 1

HCID 66619734HCID 66619734, compound

Product 1

HCID 59402678HCID 59402678, compoundYield 174.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 2631-ButanolSolvent

Procedure

4-[3-(Aminocarbonyl)-2,4-difluorophenoxy]-2-butenoic acid (100 mg, 0.32 mmol) was stirred with 5% Rh/C (5 mg) in butanol (5 ml) under H2, at r.t. for 21 h. The reaction mixture was filtered through a pad of celite and rinsed with CH2Cl2 (3×5 ml). The filtrate was evaporated to dryness, under reduced pressure, to give 88 mg of the desired product, yield 87%, mp 53-55° C. HPLC-MS (method 1): m/z 316 [M+H]+, Rt=3.49 min.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washrinsed with CH2Cl2 (3×5 ml)
  3. customThe filtrate was evaporated to dryness, under reduced pressure

Sources & evidence

ORD record
ord-365d3e23a690431a94331d58fee52241
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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