Benzyl mercaptan → tert-Butyl [2-(benzylsulfanyl)ethyl]carbamate

HRID 2421617Notes

Reaction equation

HRID 2421617 reaction equation
[C:1]([NH:8][CH2:9][CH2:10]S(C1C=CC(C)=CC=1)(=O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:21]([SH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:1]([NH:8][CH2:9][CH2:10][S:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 10796Cesium carbonateHCID 67213765HCID 67213765, compound

Product 1

HCID 29973008tert-Butyl [2-(benzylsulfanyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Boc-2-Tosyl-ethylamine (100 mg, 0.32 mmol) was added to a mixture of benzylmercaptan (45 mL, 0.38 mmol) and Cs2CO3 (68 mg, 0.21 mmol) in 1.6 mL of dry DMF. The reaction was stirred for 18 hours after which time the reaction mixture was poured onto water. The aqueous layer was extracted three times with AcOEt. The combined organic layers were washed with water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated. The residue was purified using SiO2 with AcOEt/Petroleum ether 5:95 to 15:75. A yellow oil was obtained (72 mg, 83%). NMR 1H (ppm, CDCl3): 7.31-7.25 (m, 5H), 4.79 (br. s., 1H), 3.70 (s, 2H), 3.25 (m, 2H), 2.55-2.53 (m, 2H), 1.43 (s, 9H).

Workup

  1. additionwas poured onto water
  2. extractionThe aqueous layer was extracted three times with AcOEt
  3. washThe combined organic layers were washed with water, saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customA yellow oil was obtained (72 mg, 83%)

Sources & evidence

ORD record
ord-961abea0e75a4840aa910da5701de036
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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