m-Chloroperbenzoic acid → benzyl (2R)-2-benzyl-5-tert-butylsulfinyl-4-oxopentanoate

HRID 973504Notes

Reaction equation

HRID 973504 reaction equation
[CH2:1]([C@H:8]([CH2:19][C:20](=[O:27])[CH2:21][S:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)Cl>[CH2:1]([C@H:8]([CH2:19][C:20](=[O:27])[CH2:21][S:22]([C:23]([CH3:24])([CH3:26])[CH3:25])=[O:36])[C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15018115Benzyl (2R)-2-Benzyl-5-tert-butylmercapto-4-oxopentanoate

Product 1

HCID 15018116benzyl (2R)-2-benzyl-5-tert-butylsulfinyl-4-oxopentanoateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The resultant compound from Example 37 (44.4 mg, 0.115 mmol) in CH2Cl2 (2 ml) at -10° C. was treated with meta-chloroperbenzoic acid (25.0 mg, 0.116 mmol, 80% pure). After 2 h at -10°-0° C. the solvent was evaporated and the residue was dissolved in ethyl acetate which was washed with 1:1 10% Na2SO4 solution/ saturated NaHCO3 solution, saturated NaHCO3 solution and brine, and then dried over Na2SO4 and evaporated to afford 46.0 mg (99%) of a colorless oil. 1H NMR (CDCl3) δ7.05-7.40 (m,10H), 5.08 (m,2H), 3.36-3.53 (m,2H), 3.30 (m,1H), 2.95-3.18 (m,2H), 2.80 (2dd,total 1H), 2.69 (2dd,total 1H), 1.24 (s,9H).

Workup

  1. customAfter 2 h at -10°-0° C. the solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate which
  3. washwas washed with 1:1 10% Na2SO4 solution/ saturated NaHCO3 solution, saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-5ef1627a1da44bd698cb7b88d9386ee0
Source dataset
uspto-grants-1991_11
Patent number
US05063208

Reaction notes

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