m-Chloroperbenzoic acid → HCID 57295905, compound

HRID 2164587Notes

Reaction equation

HRID 2164587 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][CH:13]2[CH:10]([C:11](=[O:15])[CH2:12]2)[C:9]=1[C:16]([O:18][CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:17])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:38])C=1>C(Cl)Cl>[C:1]([NH:4][CH2:5][CH2:6][S:7]([C:8]1[CH2:14][CH:13]2[CH:10]([C:11](=[O:15])[CH2:12]2)[C:9]=1[C:16]([O:18][CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:38])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57219839HCID 57219839, compound

Product 1

HCID 57295905HCID 57295905, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 60 mg of 3-(2'-acetamidoethylthio)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, 1-naphthylmethyl ester, in 10 mL of methylene chloride at -50° under argon was added a solution of 32 mg of m-chloroperbenzoic acid in 3 mL of methylene chloride in one portion. This solution was stirred for 30 min at -40° and then allowed to warm to room temperature over a 30 min period. The methylene chloride solution was washed sequentially with aqueous sodium sulfite and aqueous sodium bicarbonate (2X), dried over sodium sulfate and evaporated to dryness. The crude product was purified by preparative thin layer chromatography on a 20×20×0.2 cm silica gel plate, eluted with 5% methanol in methylene chloride, to afford 55 mg (88%) of 3-(2'acetamidoethylsulfinyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, 1-naphthylmethyl ester, as a glassy mixture of 2 diastereoisomers (at sulfur). IR (Nujol mull): 3250, 1785, 1715, 1670 cm-1 ; NMR (220 MHz; CDCl3): δ 1.93 (3H, s), 2.8-3.7 (9H, m), 4.66 (1H, m), 5.5-5.75 (2H, m), 6.48 (1H, m), and 7.3-1.1 (7H, m); MS (field desorption) confirmed molecular weight of 425. ##STR23##

Workup

  1. washThe methylene chloride solution was washed sequentially with aqueous sodium sulfite and aqueous sodium bicarbonate (2X)
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by preparative thin layer chromatography on a 20×20×0.2 cm silica gel plate
  5. washeluted with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-5d09b601cb904f7eb532e0e759fb268b
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

Loading…