Methyl formate → HCID 70480530, compound

HRID 462897Notes

Reaction equation

HRID 462897 reaction equation
[Cl:1][CH:2]1[N:5]([CH:6]([C:23]([CH3:25])=[CH2:24])[C:7]([O:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C:4](=[O:26])[CH:3]1[NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OC)=O.[Cl:42]OC(C)(C)C>C(OCC)(=O)C>[Cl:1][CH:2]1[N:5]([CH:6]([C:23]([CH2:25][Cl:42])=[CH2:24])[C:7]([O:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[C:4](=[O:26])[CH:3]1[NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 521297Tert-Butyl hypochloriteHCID 12416138HCID 12416138, compound

Product 1

HCID 70480530HCID 70480530, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 5.18 g. portion of diphenylmethyl 2-(4-chloro-3-phenoxyacetamido-2-oxo-1-azetidinyl)-3-methyl-3-butenoate was dissolved in 200 ml. of methyl formate, and 1.71 ml. of t-butyl hypochlorite was added. The mixture was stirred at room temperature for 16 hours. It was then evaporated under vacuum to obtain a white foam, which was taken up in ethyl acetate and washed three times with water. The organic layer was then decolorized with activated carbon, dried over magnesium sulfate, and evaporated to a white foam. The foam was taken up in 100 ml. of dry diethyl ether, from which 1.12 g. of the desired product was obtained in crystalline form. The product was analyzed by infrared in chloroform, showing maxima at 1795, 1745 and 1695 cm-1 ; a second spectrum in methanol showed maxima at 1775, 1740 and 1695 cm-1. NMR analysis on a 100 megacycle instrument in CDCl3 showed the following 6 values. 4.24(s); 4.63(s); 5.73(center of q); 6.2(d); 5.09(s); 5.33(s); 5.5(s)

Workup

  1. customIt was then evaporated under vacuum
  2. customto obtain a white foam, which
  3. washwashed three times with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to a white foam

Sources & evidence

ORD record
ord-eaf1cf5122074e33a3150c705113f736
Source dataset
uspto-grants-1985_05
Patent number
US04518531

Reaction notes

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