m-Chloroperbenzoic acid → N-BOC 1-amino-2-chloro-3-(p-nitrophenyl)sulfinylpropane

HRID 2166753Notes

Reaction equation

HRID 2166753 reaction equation
[C:1]([NH:8][CH2:9][CH:10]([Cl:22])[CH2:11][S:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)Cl>[C:1]([NH:8][CH2:9][CH:10]([Cl:22])[CH2:11][S:12]([C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)=[O:31])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13135212N-BOC 1-amino-2-chloro-3-(p-nitrophenyl)thiopropane

Product 1

HCID 53988848N-BOC 1-amino-2-chloro-3-(p-nitrophenyl)sulfinylpropane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

The product from Step B, 2.II, 207 mg, in 9 ml of CH2Cl2 is treated dropwise at 0° C. over 70 minutes with 121 mg of m-chloroperbenzoic acid (MCPBA) (85%) in 9 ml of CH2Cl2 under N2. The solution is stirred 1 hour at 25° C., washed with aqueous NaHCO3, dried with MgSO4, filtered, evaporated (209 mg) and purified by preparative thin layer chromatography on silica gel with 4:1 (v/v) CHCl3 -ethylacetate, affording 97 mg of pure product, Rf 0.25.

Workup

  1. washwashed with aqueous NaHCO3
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated (209 mg)
  5. custompurified by preparative thin layer chromatography on silica gel with 4:1 (v/v) CHCl3 -ethylacetate

Sources & evidence

ORD record
ord-7402f6d22c854e3f8c9621e4348c0756
Source dataset
uspto-grants-1983_06
Patent number
US04388475

Reaction notes

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