Water → HCID 66799696, compound

HRID 2172728Notes

Reaction equation

HRID 2172728 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:13]3[N:18]=[C:17]([C:19]([NH2:21])=[O:20])[CH:16]=C(C=C)[CH:14]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.[CH3:26][CH:27]([OH:29])[CH3:28].[OH2:30]>>[OH:29][C@H:27]([C:28]1[CH:14]=[C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]3[CH:24]=[CH:25][C:2]([F:1])=[CH:3][CH:4]=3)[CH:8]=2)[N:18]=[C:17]([C:19]([NH2:21])=[O:20])[CH:16]=1)[CH2:26][OH:30]

Participants

4

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 66799599HCID 66799599, compound

Product 1

HCID 66799696HCID 66799696, compoundYield 26%

Procedure

To a scintillation vial was added 6-[3-(4-fluoro-phenoxy)-phenyl]-4-vinyl-pyridine-2-carboxylic acid amide (0.066 g), 5 ml IPA, 5 ml water, and 0.270 g AD Mix beta. After the oxidation reaction was complete, the mixture was partitioned between 50 ml water and 50 ml EtOAc. The organic layer was separated, concentrated under reduced vacuum, and chromatographed by combiflash using a 12-gram silica column using a gradient of MeOH (0-40%) in chloroform as the eluent. The compound was purified further by prep TLC (100% EtOAc) followed by crystallization from chloroform and hexane to provide 0.019 g of 4-((R)-1,2-dihydroxy-ethyl)-6-[3-(4-fluoro-phenoxy)-phenyl]-pyridine-2-carboxylic acid amide as a white solid (26% yield) in very high purity. 1H NMR (CHCl3) 8.80-8.73 (m, 1 H), 8.22-8.14 (m, 1 H), 7.79-7.74 (m, 1 H), 7.71-7.64 (m, 1 H), 7.56-7.47 (s, 1 H), 7.31-7.03 (m, 7 H), 5.55-5.47 (m, 1 H), 4.86-4.80 (m, 1 H), 4.77-4.69 (m, 1 H), 3.55-3.44 (m, 1H). LC/MS: m/z=368[M]+.

Workup

  1. additionMix beta
  2. customAfter the oxidation reaction
  3. customthe mixture was partitioned between 50 ml water and 50 ml EtOAc
  4. customThe organic layer was separated
  5. concentrationconcentrated under reduced vacuum
  6. customchromatographed by combiflash
  7. customThe compound was purified further by prep TLC (100% EtOAc)
  8. customfollowed by crystallization from chloroform and hexane

Sources & evidence

ORD record
ord-7f838729a0804b238278b28d4b34ea12
Source dataset
uspto-grants-2015_06
Patent number
US09056832B2

Reaction notes

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