alpha-Chlorohydrin, (+)- → HCID 68628850, compound

HRID 2037358Notes

Reaction equation

HRID 2037358 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH:17]=[C:16]([CH3:24])[N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[OH:26])[CH3:2].Cl[CH2:28][C@@H:29]([OH:32])[CH2:30][OH:31]>C(O)(C)C.[OH-].[Na+].O>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH:17]=[C:16]([CH3:24])[N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[O:26][CH2:28][C@@H:29]([OH:32])[CH2:30][OH:31])[CH3:2]

Participants

6

Reactant 2

HCID 148904alpha-Chlorohydrin, (+)-2×HCID 136344049HCID 136344049, compound

Product 1

HCID 68628850HCID 68628850, compoundYield 32.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 2-ethyl-4-[5-(4-isobutyl-6-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenol (41 mg, 0.116 mmol) in isopropanol (3 mL) and 3 N aq. NaOH (0.4 mL), (S)-3-chloro-1,2-propanediol (66 mg, 0.577 mmol) is added. The mixture is stirred at 65° C. for 16 h before another portion of (S)-3-chloro-1,2-propanediol (66 mg, 0.577 mmol) and 3 N aq. NaOH (0.4 mL) is added. Stirring is continued at 65° C. for 24 h. The mixture is cooled to rt, diluted with water, and repeatedly extracted with diethyl ether. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC using DCM:methanol 9:1 to give the title compound (16 mg) as a colourless oil; LC-MS: tR=1.02 min, [M+H]+=426.17.

Workup

  1. additionis added
  2. extractionrepeatedly extracted with diethyl ether
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-2dd74b0199bf4e3fbdc27bc1e0d47b7f
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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