HCID 22915344, compound → HCID 22915337, compound

HRID 1377773Notes

Reaction equation

HRID 1377773 reaction equation
C([C:4]1[C:5]([O:16][CH2:17][C:18]([Cl:20])=[CH2:19])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11](=[O:14])[CH:10]=[C:9]2[CH3:15])(=O)C.ClC(=C)[CH2:23][O:24]C1C(O)=C2C(C(C)=CC(=O)O2)=CC=1>>[Cl:20][C:18](=[CH2:19])[CH2:17][O:16][C:5]1[C:4]([O:24][CH3:23])=[C:13]2[C:8]([C:9]([CH3:15])=[CH:10][C:11](=[O:14])[O:12]2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 22915344HCID 22915344, compoundHCID 22915349HCID 22915349, compound

Product 1

HCID 22915337HCID 22915337, compound

Procedure

As shown in FIG. 24, the synthesis pathway for the compounds of the present invention involves starting with the following compound, Compound 1: ##STR5## This starting compound in the synthesis of Compound 2 is 4,5'-dimethyl-8-methoxypsoralen. The synthesis of this precursor compound has been described previously in the literature. See Bender, et al., J. Org. Chem. 44:2176 (1979). Alternatively, the starting compound may be synthesized by the following method: 8-acetyl-7-(2-chloroallyl)oxy-4-methylcoumarin, described in Bender, et al., J. Org. Chem. 48:2709 (1983), is initially oxidized to a phenolic compound, 7-(2-chloro-2-propenyl)oxy-8-hydroxy-4-methylcoumarin, and then methylated, providing 7-(2-chloro-2-propenyl)oxy-8-methoxy-4-methylcoumarin. Claisen rearrangement provides 6-(2-chloro-2-propenyl)-7-hydroxy-8-methoxy-4-methylcoumarin, which is then converted to 4,5'-dimethyl-8-methoxypsoralen.

Workup

  1. customThe synthesis of this precursor compound
  2. customAlternatively, the starting compound may be synthesized by the following method

Sources & evidence

ORD record
ord-00fb6a105f0b44a4aa6949a514e3735b
Source dataset
uspto-grants-1997_09
Patent number
US05665762

Reaction notes

Loading…