Dimethylformamide → HCID 20189646, compound

HRID 1789039Notes

Reaction equation

[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH2:10]/[CH:11]=[C:12](/[CH2:14][CH2:15]C(O)=O)\[CH3:13])[C:5]([OH:19])=[C:4]2[C:20]([O:22][CH2:23][C:3]=12)=[O:21].S(Cl)(Cl)=O.CN(C)C=[O:31].Cl[CH2:34][Cl:35]>>[OH:19][C:5]1[C:6]([CH:10]([CH2:11]/[C:12](/[CH3:13])=[CH:14]/[CH3:15])[C:34]([Cl:35])=[O:31])=[C:7]([O:8][CH3:9])[C:2]([CH3:1])=[C:3]2[C:4]=1[C:20](=[O:21])[O:22][CH2:23]2

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6344Dichloromethane

HCID 24386Thionyl Chloride

HCID 446541Mycophenolic Acid

Product 1

HCID 20189646HCID 20189646, compound

Procedure

A solution of 500 mgs of mycophenolic acid in 10 ml of dichloromethane containing 0.5 ml of thionyl chloride and 0.05 ml of N.N-dimethylformamide was maintained at 25° C. for 3 hours. The volatile components were then distilled off under vacuum to obtain crude (E)-[1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoyl chloride.

Workup

distillationThe volatile components were then distilled off under vacuum

Sources & evidence

ORD record: ord-cf1a75afa44e49b2a2f9d4faab45e775
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04686234

Reaction notes

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