Acetic Acid → HCID 20478387, compound

HRID 904702Notes

Reaction equation

HRID 904702 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=[C:7]2[S:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:3])[CH3:2].[CH2:29]([O:31][C:32](=[O:38])[C:33](OCC)=O)[CH3:30].CCOCC.C(O)(=O)C>CN(C)C=O.[Cl-].[Na+].O.O1CCOCC1>[CH3:21][O:20][C:18]([C:9]1[CH:8]=[C:7]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]3[O:14][C:33]([C:32]([O:31][CH2:29][CH3:30])=[O:38])=[CH:2][C:1](=[O:3])[C:4]=3[CH:5]=2)[N:10]=1)=[O:19]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 7268Diethyl OxalateHCID 135773207HCID 135773207, compound

Product 1

HCID 20478387HCID 20478387, compoundYield 31.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of the product of step (a) (4.0 g) and diethyloxalate (13.0 g) in dry dimethylformamide (275 ml) was slowly added to a stirred suspension of ether washed sodium hydride (50% dispersion in oil, 2.1 g) in dry dimethylformamide (225 ml) under an atmosphere of nitrogen. The resulting suspension was stirred for 1 week then poured into water (1000 ml). The solution formed was acidified with glacial acetic acid, made saline with brine, extracted with ethyl acetate (2×500 ml), washed with water, dried and evaporated to give a brown oil. This oil was dissolved in dry dioxan and dry hydrogen chloride gas was bubbled through it for 15 minutes. The solution was then poured into water, extracted with ethyl acetate (2×300 ml), dried and evaporated to give a yellow brown solid which gave the sub-title compound (1.5 g) after chromatography (SiO2 /3:2 40°-60° petroleum ether/ether) as yellow crystals.

Workup

  1. washwashed sodium hydride (50% dispersion in oil, 2.1 g) in dry dimethylformamide (225 ml) under an atmosphere of nitrogen
  2. additionthen poured into water (1000 ml)
  3. customThe solution formed
  4. extractionextracted with ethyl acetate (2×500 ml)
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customto give a brown oil
  9. customdry hydrogen chloride gas was bubbled through it for 15 minutes
  10. additionThe solution was then poured into water
  11. extractionextracted with ethyl acetate (2×300 ml)
  12. customdried
  13. customevaporated
  14. customto give a yellow brown solid which

Sources & evidence

ORD record
ord-4be03af53f314829a5d1e494a975f592
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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