Phosphorus oxychloride → HCID 86614931, compound

HRID 1820287Notes

Reaction equation

HRID 1820287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:25])[CH2:13][CH2:12][CH:11]([C:14](=[O:22])[C@@H:15]([NH:19][CH:20]=O)[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:24])[CH3:23])=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]2([OH:25])[CH2:13][CH2:12][CH:11]([C:14](=[O:22])[C@@H:15]([N+:19]#[C-:20])[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:23])[CH3:24])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86614932HCID 86614932, compound

Product 1

HCID 86614931HCID 86614931, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a mixture of N-((2S)-1-((4R)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylcyclohexyl)-3-methyl-1-oxobutan-2-yl)formamide (109 mg, 0.298 mmol) and TEA (0.208 mL, 1.490 mmol) in CH2Cl2 (5 mL) was added POCl3 (0.027 mL, 0.298 mmol) at 0° under N2. The mixture was stirred at 0-5° C. for 3 h. The mixture was quenched with NaHCO3(aq), extracted into CH2Cl2, and dried over Na2SO4. After concentrating, the crude residue was purified via column chromatography (CH2Cl2) to give (2S)-1-((4R)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylcyclohexyl)-2-isocyano-3-methylbutan-1-one (85 mg, 0.244 mmol, 82% yield) as a light yellow oil.

Workup

  1. customThe mixture was quenched with NaHCO3(aq)
  2. extractionextracted into CH2Cl2
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrating
  5. customthe crude residue was purified via column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-1f1a6a432f7547399065b306adbb3a82
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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