Water → HCID 21715989, compound

HRID 1084433Notes

Reaction equation

HRID 1084433 reaction equation
[OH:1][CH:2]([CH2:7][CH:8](O)/[CH:9]=[CH:10]/[C:11]1[N:12]([CH:29]([CH3:31])[CH3:30])[C:13](=[O:28])[C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:3][C:4]([OH:6])=[O:5].C1(N=C=NC2CCCCC2)CCCCC1.O>ClCCl>[OH:1][CH:2]1[CH2:7][CH:8](/[CH:9]=[CH:10]/[C:11]2[N:12]([CH:29]([CH3:31])[CH3:30])[C:13](=[O:28])[C:14]3[C:19]([C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:5][C:4](=[O:6])[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 20063332HCID 20063332, compound

Product 1

HCID 21715989HCID 21715989, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of a 1:1 mixture of the erythro- and threo-diastereoisomers of (E)-3,5-dihydroxy-7-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]hept-6-enoic acid (0.35 g; prepared as described in Example 5) in dichloromethane (25 ml) was treated with dicyclohexylcarbodiimide (0.18 g) and the resulting solution was stirred at room temperature for 1 hour. The solution was treated with water (20 ml), and stirred for 30 minutes. The layers were then separated and the aqueous phase was extracted with dichloromethane (210 ml). The combined extracts were dried over magnesium sulphate and evaporated to dryness. The resulting residue was triturated with diethyl ether (10 ml) and the insoluble material was filtered off. Evaporation of the ethereal solution gave a pale yellow solid, which was triturated with petroleum ether (b.p. 60°-80° C.; 10 ml) and filtered, to give (E)-4-hydroxy-6-[2-{4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl}ethenyl]-3,4,5,6-tetrahydro-2H-pyran-2-one, in the form of a pale yellow solid (0.21 g), m.p. 151°-154° C. [Elemental analysis: C, 70.8; H, 5.74; N, 3.35%; calculated: C, 71.24; H, 5.74; N, 3.32%].

Workup

  1. stirringstirred for 30 minutes
  2. customThe layers were then separated
  3. extractionthe aqueous phase was extracted with dichloromethane (210 ml)
  4. dry with materialThe combined extracts were dried over magnesium sulphate
  5. customevaporated to dryness
  6. customThe resulting residue was triturated with diethyl ether (10 ml)
  7. filtrationthe insoluble material was filtered off
  8. customEvaporation of the ethereal solution
  9. customgave a pale yellow solid, which
  10. customwas triturated with petroleum ether (b.p. 60°-80° C.; 10 ml)
  11. filtrationfiltered

Sources & evidence

ORD record
ord-dc42b340d1be4af9b703b321f63c5844
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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