Dicyclohexylcarbodiimide → morpholinoethyl E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

HRID 4504

Reaction equation

HRID 4504 reaction equation
[C:1]([O:4][C:5]1[C:13]([CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:12]([O:23][CH3:24])[C:11]([CH3:25])=[C:10]2[C:6]=1[C:7](=[O:26])[O:8][CH2:9]2)(=[O:3])[NH2:2].C1(N=C=NC2CCCCC2)CCCCC1.O[CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>C1COCC1>[C:1]([O:4][C:5]1[C:13]([CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][C:19]([O:21][CH2:43][CH2:44][N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)=[O:20])=[C:12]([O:23][CH3:24])[C:11]([CH3:25])=[C:10]2[C:6]=1[C:7](=[O:26])[O:8][CH2:9]2)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 611632-MorpholinoethanolHCID 67854275E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid

Product 1

HCID 67854272morpholinoethyl E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.0 g of E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid dissolved in 20 ml of dry THF is added 0.59 g of dicyclohexylcarbodiimide and 0.037 g of N-(2-hydroxyethyl)morpholine. The mixture is left at room temperature for 6 hours, then evaporated to dryness. The residue is chromatographed on silica gel, eluting with 50:1 dichloromethane:methanol, to give morpholinoethyl E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate.

Workup

  1. customevaporated to dryness
  2. customThe residue is chromatographed on silica gel
  3. washeluting with 50:1 dichloromethane

Sources & evidence

ORD record
ord-8099b77f8ff84220a75161afb1f5b51b
Source dataset
uspto-grants-1988_02
Patent number
US04727069

Linked notes

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