Toluene → Benzyl (2R)-2-Benzyl-5-tert-butylmercapto-4-oxopentanoate

HRID 973503Notes

Reaction equation

HRID 973503 reaction equation
[C:1]([SH:5])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[CH2:23]([C@H:30]([CH2:41][C:42]([CH2:44]Cl)=[O:43])[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:23]([C@H:30]([CH2:41][C:42](=[O:43])[CH2:44][S:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6387tert-Butyl mercaptanHCID 3251421Potassium bis(trimethylsilyl)amideHCID 10449338Benzyl (2R)-2-Benzyl-3-chloromethylcarbonylpropionate

Product 1

HCID 15018115Benzyl (2R)-2-Benzyl-5-tert-butylmercapto-4-oxopentanoateYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To tert-butylmercaptan (0.11 ml) in dimethylformamide (5 ml) at 0° C. was added potassium bis(trimethylsilyl)amide in toluene (1.80 ml, 0.90 mmol, 0.5M) followed by the resultant compound from Example 34 (259.6 mg, 0.785 mmol) in dimethylformamide (3 ml). After 16 h at room temperature the mixture was diluted with ethyl acetate, washed with water and brine, then dried over Na2SO4 and evaporated. Chromatography of the residue on silica gel with 10% ethyl acetate in hexane afforded 219.6 mg (73%) of a colorless oil. 1H NMR (CDCl3) δ7.10-7.40 (m,10H), 5.07 (s,2H), 3.25 (s,2H), 3.18-3.29 (m,1H), 2.97-3.07 (m,2H), 2.78 (dd,1H), 2.71 (dd,1H), 1.25 (s,9H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-3b137e8635dc419084ff4b5fb4c72d5d
Source dataset
uspto-grants-1991_11
Patent number
US05063208

Reaction notes

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