Sodium Hypochlorite → tert-butyl ((S)-3-cyclohexyl-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)carbamate

HRID 58834Notes

Reaction equation

HRID 58834 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:9](=[O:13])[C:10]([CH3:12])=[CH2:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O-:22]Cl.[Na+]>CN(C=O)C.O.CCOC(C)=O>[CH:1]1([CH2:7][C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:9]([C@@:10]2([CH3:12])[CH2:11][O:22]2)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 23665760Sodium Hypochlorite2×HCID 117608154(S)-tert-butyl (1-cyclohexyl-4-methyl-3-oxopent-4-en-2-yl)carbamate

Product 1

HCID 117608155tert-butyl ((S)-3-cyclohexyl-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)carbamateYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (S)-tert-butyl (1-cyclohexyl-4-methyl-3-oxopent-4-en-2-yl)carbamate (5.36 g, 18.1 mmol) in DMF at −10° C. was added NaOCl (47.1 mL of a 9.5% w/w solution, 36.2 mmol). Addition of NaOCl was performed at a rate to maintain an internal temperature of ≦−10° C. After the addition was complete the reaction mixture was transferred to an ice bath and stirred for an additional 2 h at which time it was diluted with water and EtOAc, extracted with EtOAc (2×), washed with brine, dried with sodium sulfate, filtered, and concentrated. Purification by column chromatography (3:1 heptane/EtOAc) provided tert-butyl ((S)-3-cyclohexyl-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)carbamate (3.68 g, 65%) as a colorless amorphous solid. MS (EI) for C17H29NO4, found 310.2 (MH−).

Workup

  1. temperatureto maintain an internal temperature of ≦−10° C
  2. additionAfter the addition
  3. customwas transferred to an ice bath
  4. extractionextracted with EtOAc (2×)
  5. washwashed with brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography (3:1 heptane/EtOAc)

Sources & evidence

ORD record
ord-11572b5fc0a24b85912e8a45c7d46bdc
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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