Triethylamine → HCID 86749563, compound

HRID 260116Notes

Reaction equation

HRID 260116 reaction equation
C([C:4]1[C:12]([CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:11]([CH2:23][CH3:24])[C:10]([CH3:25])=[C:9]2[C:5]=1[C:6](=[O:26])[O:7][CH2:8]2)(O)=O.C([N:29]([CH2:32]C)CC)C.C1([O:40]P(Cl)(OC2C=CC=CC=2)=O)C=CC=CC=1.[N-]=[N+]=[N-].[Na+]>CN(C)C=O>[CH2:23]([C:11]1[C:10]([CH3:25])=[C:9]2[C:5]([C:6](=[O:26])[O:7][CH2:8]2)=[C:4]([N:29]=[C:32]=[O:40])[C:12]=1[CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH3:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 75654Diphenyl chlorophosphateHCID 86749562HCID 86749562, compound

Product 1

HCID 86749563HCID 86749563, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, 0° C. solution of 6.0 g of methyl (E)-6-(4-carboxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate in 150 ml of dimethylformamide is added 4.62 ml of triethylamine followed by dropwise addition of 4.5 ml of diphenylchlorophosphate. The mixture is allowed to stir at room temperature for 1 hour and then recooled to 0° C., and treated with 10.8 g of sodium azide. This mixture is stirred for 24 hours at 0° C. and then partitioned between aqueous sodium hydrogen sulfate and ethyl acetate. The organic phase is washed four times with water, dried over magnesium sulfate, and concentrated under reduced pressure to give methyl (E)-6-(1,3-dihydro-6-ethyl-4-isocyanato-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate.

Workup

  1. customrecooled to 0° C.
  2. stirringThis mixture is stirred for 24 hours at 0° C.
  3. custompartitioned between aqueous sodium hydrogen sulfate and ethyl acetate
  4. washThe organic phase is washed four times with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-306e5844cc8846b592267d331812650b
Source dataset
uspto-grants-1996_06
Patent number
US05525602

Reaction notes

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