1-((1S)-1-isocyanatoethyl)naphthalene → (1-Naphthalen-1-yl-ethyl)-carbamic acid-4-benzo [1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-5-oxo-3-(3,4,5-trimethoxy-benzyl)-2,5-dihydro-furan-2-yl ester

HRID 582090Notes

Reaction equation

HRID 582090 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11](=[O:37])[O:12][C:13]([OH:36])([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C:14]=3[CH2:15][C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[C:38]1([C@@H:48]([N:50]=[C:51]=[O:52])[CH3:49])[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1>CN(C)C1C=CN=CC=1.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11](=[O:37])[O:12][C:13]([O:36][C:51](=[O:52])[NH:50][CH:48]([C:38]4[C:47]5[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=5)[CH:41]=[CH:40][CH:39]=4)[CH3:49])([C:28]4[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=4)[C:14]=3[CH2:15][C:16]3[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 70235101-((1S)-1-isocyanatoethyl)naphthaleneHCID 9870830CI 1020

Product 1

HCID 15411000(1-Naphthalen-1-yl-ethyl)-carbamic acid-4-benzo [1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-5-oxo-3-(3,4,5-trimethoxy-benzyl)-2,5-dihydro-furan-2-yl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 15 mL dichloromethane was added 3-benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxyphenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one 1.00 g (1.98 mmol) and stirred to dissolve. To this was added (S)-1-(1-naphthyl)ethyl isocyanate 414 mg (2.1 mmol) and a catalytic amount of 4-dimethylaminopyridine 20 mg (0.164 mmol). The mixture was stirred at room temperature for 24 hours. The solution was washed with 50 mL water and 50 mL brine, and the organic phase was separated and dried over magnesium sulfate, then evaporated to dryness. The crude product was then purified by flash chromatography (150 g silica gel, 10% EtOAc/CH2Cl2). The product was isolated by evaporation of the appropriate fractions to give 840 mg (60%) as a white foam. The product was identified by 1H NMR, MS, [M+H]+ =704 Da. and microanalysis.

Workup

  1. dissolutionto dissolve
  2. stirringThe mixture was stirred at room temperature for 24 hours
  3. washThe solution was washed with 50 mL water and 50 mL brine
  4. customthe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe crude product was then purified by flash chromatography (150 g silica gel, 10% EtOAc/CH2Cl2)
  8. customThe product was isolated by evaporation of the appropriate fractions
  9. customto give 840 mg (60%) as a white foam

Sources & evidence

ORD record
ord-32c35bab1d40449c8ec5981052b0d01d
Source dataset
uspto-grants-1999_07
Patent number
US05922759

Reaction notes

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