8-Oxo-2,2,5,7-tetramethyl-7-(1-o-nitrobenzylcarbonyldioxymethyl)-3-oxa-1-azabicyclo[4.2.0]octane → 3-Methyl-1-(2-tetrahydropyranyl)-3-(o-nitrobenzylcarbonyldioxymethyl)-4-[1-methyl-2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone

HRID 1706153Notes

Reaction equation

HRID 1706153 reaction equation
O=C1N2C(C(C)COC2(C)C)C1(C)CO[O:15][C:16]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])=[O:17].O=C1N2C(C(C)COC2(C)C)C1(C)CO.[CH3:44][C:45]1([CH2:66][OH:67])[CH:48]([CH:49]([CH3:58])[CH2:50][O:51][CH:52]2[CH2:57][CH2:56][CH2:55][CH2:54][O:53]2)[N:47]([CH:59]2[CH2:64][CH2:63][CH2:62][CH2:61][O:60]2)[C:46]1=[O:65]>>[CH3:44][C:45]1([CH2:66][O:67][O:17][C:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])=[O:15])[CH:48]([CH:49]([CH3:58])[CH2:50][O:51][CH:52]2[CH2:57][CH2:56][CH2:55][CH2:54][O:53]2)[N:47]([CH:59]2[CH2:64][CH2:63][CH2:62][CH2:61][O:60]2)[C:46]1=[O:65]

Participants

4

Reactant 3

HCID 203373778-Oxo-2,2,5,7-tetramethyl-7-(1-o-nitrobenzylcarbonyldioxymethyl)-3-oxa-1-azabicyclo[4.2.0]octaneHCID 204494488-Oxo-2,2,5,7-tetramethyl-7-(hydroxymethyl)-3-oxa-1-azabicyclo[4.2.0]octaneHCID 233330253-Methyl-1-(2-tetrahydropyranyl)-3-(hydroxymethyl)-4-[1-methyl-2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone

Product 1

HCID 203373763-Methyl-1-(2-tetrahydropyranyl)-3-(o-nitrobenzylcarbonyldioxymethyl)-4-[1-methyl-2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone

Procedure

Following the procedure described for the preparation of 8-oxo-2,2,5,7-tetramethyl-7-(1-o-nitrobenzylcarbonyldioxymethyl)-3-oxa-1-azabicyclo[4.2.0]octane from 8-oxo-2,2,5,7-tetramethyl-7-(1-hydroxymethyl)-3-oxa-1-azabicyclo[4.2.0]octane and using 3-methyl-1-(2-tetrahydropyranyl)-3-(hydroxymethyl)-4-[1-methyl-2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone there is obtained 3-methyl-1-(2-tetrahydropyranyl)-3-(o-nitrobenzylcarbonyldioxymethyl)-4-[1-methyl-2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone.

Sources & evidence

ORD record
ord-8dfa4ffa18334e2b89da226c6a8a2122
Source dataset
uspto-grants-1980_06
Patent number
US04206219

Reaction notes

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