Ethyl 3-acetyl-1,2,3,4-tetrahydro-4-(2-(p-methoxybenzylthio)-5-nitrophenyl)-6-methyl-2-oxo-5-pyrimidine carboxylate → Ethyl 5-acetyl-3,4,5,6-tetrahydro-2-methyl-8-nitro-4-oxo-2,6-methano-2H-1,3,5-benzothiadiazocine-11-carboxylate

HRID 64594Notes

Reaction equation

HRID 64594 reaction equation
[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[S:19]CC2C=CC(OC)=CC=2)[C:8]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:7]([CH3:34])[NH:6][C:5]1=[O:35])(=[O:3])[CH3:2].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[C:1]([N:4]1[CH:9]2[CH:8]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:7]([CH3:34])([S:19][C:11]3[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=32)[NH:6][C:5]1=[O:35])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 20236389Ethyl 3-acetyl-1,2,3,4-tetrahydro-4-(2-(p-methoxybenzylthio)-5-nitrophenyl)-6-methyl-2-oxo-5-pyrimidine carboxylateHCID 66633105Anisole trifluoroacetic acid

Product 1

HCID 20236387Ethyl 5-acetyl-3,4,5,6-tetrahydro-2-methyl-8-nitro-4-oxo-2,6-methano-2H-1,3,5-benzothiadiazocine-11-carboxylate

Procedure

The compound 2b is treated with anhydrous trifluoroacetic acid:anisole (1:1) at 25° C. for 1 hour to yield a mixture of the diastereomers of the desired product. The individual diastereomers may be separated by chromatography.

Workup

  1. customto yield

Sources & evidence

ORD record
ord-9e093d8c22bc41a8ac9f53cb929ef0ae
Source dataset
uspto-grants-1986_09
Patent number
US04609494

Reaction notes

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