m-Chloroperbenzoic acid → HCID 76483165, compound

HRID 2290515Notes

Reaction equation

HRID 2290515 reaction equation
Cl.[CH2:2]([O:4][C:5]([CH:7]([NH:16][CH:17]1[C:23](=[O:24])[N:22]2[CH:25]([C:28]([OH:30])=[O:29])[CH2:26][S:27][CH:21]2[CH2:20][CH2:19][CH2:18]1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:36]>C(O)C>[CH2:2]([O:4][C:5]([CH:7]([NH:16][CH:17]1[C:23](=[O:24])[N:22]2[CH:25]([C:28]([OH:30])=[O:29])[CH2:26][S:27](=[O:36])[CH:21]2[CH2:20][CH2:19][CH2:18]1)[CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 77854583HCID 77854583, compound

Product 1

HCID 76483165HCID 76483165, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of [3R-[3α,6α(S*R*),9aα]]-6-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-5-oxothiazolo[3,2-a]azepine-3-carboxylic acid hydrochloride (1 mmole) in 50 ml of absolute ethanol at 0° under nitrogen, purified meta-chloroperoxybenzoic acid (1.05 mmole) can be added. The reaction mixture can be stirred for 3 hours at 0° and then absorbed onto a Dowex 50 X-2 ion-exchange column. Elution with ethanol-water (1:1) and then 4% pyridine-water will permit recovery of the product. The product can then be freeze-dried to afford a mixture of diastereomeric sulfoxides which can be separated by preparative chromatography on a reverse-phase column.

Workup

  1. additioncan be added
  2. customabsorbed onto a Dowex 50 X-2 ion-exchange column
  3. washElution with ethanol-water (1:1)
  4. customThe product can then be freeze-dried
  5. customto afford
  6. customcan be separated by preparative chromatography on a reverse-phase column

Sources & evidence

ORD record
ord-13f52ce3552c4699820d1ebe3b203f18
Source dataset
uspto-grants-1986_10
Patent number
US04617301

Reaction notes

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