Diazomethane → HCID 54403077, compound

HRID 2254145Notes

Reaction equation

HRID 2254145 reaction equation
[CH3:1][C:2]1[N:3]([CH2:32][O:33][CH3:34])[C:4]([CH3:31])=[C:5]([C:20]([O:22]COC(=O)C(C)(C)C)=[O:21])[C@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8]([OH:10])=[O:9].[N+](=C)=[N-].[OH-].[K+].CC1N(COC)C(C)=C(C(OC)=O)[C@@H:45]([C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([N+]([O-])=O)[CH:51]=2)C=1C(O)=O.[C:67]1(C=[N+]=[N-])C=CC=CC=1>C(OCC)C.CO>[CH3:31][C:4]1[N:3]([CH2:32][O:33][CH3:34])[C:2]([CH3:1])=[C:7]([C:8]([O:10][CH3:67])=[O:9])[C@@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:5]=1[C:20]([O:22][CH2:45][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:21]

Participants

8

Reactant 5

HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 136601Benzene, (diazomethyl)-HCID 15004125HCID 15004125, compoundHCID 54056417HCID 54056417, compound

Product 1

HCID 54403077HCID 54403077, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The resulting (R)-1,4-dihydro-2,6-dimethyl-1-methoxymethyl-4-(3-nitrophenyl)5-pivaloyloxymethoxycarbonyl -3-pyridinecarboxylic acid was treated with a 0.5 M solution of diazomethane in diethyl ether and then treated with a 10% potassium hydroxide solution in methanol. The resulting (S) -1,4-dihydro-2,6-dimethyl-1-methoxymethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-3-pyridinecarboxylic acid (recrystallized) was reacted with phenyldiazomethane to obtain (R)-benzyl methyl 1,4-dihydro-2,6-dimethyl-1-methoxymethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate. As a result of HPLC (isopropanol/hexane=1/10) using CHIRALCEL OD, the optical purity was found to be 69% ee.

Sources & evidence

ORD record
ord-57644a4422cb4820bde4deb3cabbd807
Source dataset
uspto-grants-1993_08
Patent number
US05234821

Reaction notes

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