Citric Acid → HCID 10979461, compound

HRID 600892Notes

Reaction equation

HRID 600892 reaction equation
C(OP([CH2:9][C:10]([N:12]([CH2:21][C:22]([C:24]1([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:26][CH2:25]1)=O)[C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])=[O:11])(OCC)=O)C.C(O[K])(C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:30]([O:29][C:27]([C:24]1([C:22]2[CH2:21][N:12]([C@H:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH3:14])[C:10](=[O:11])[CH:9]=2)[CH2:26][CH2:25]1)=[O:28])[CH3:31]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 86591641HCID 86591641, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 10979461HCID 10979461, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After dissolving ethyl 1-[2-[N-(diethylphosphonoacetyl)-N-[1-(S)-phenylethyl]amino]acetyl]cyclopropanecarboxylate (25.0 g, 55.2 mmol) in toluene (250 ml), tert-butoxypotassium (7.40 g, 66.2 mmol) was added gradually while stirring and cooling with ice. After stirring the reaction solution for 15 minutes at room temperature, a 10% aqueous citric acid solution (250 ml) and ethyl acetate (250 ml) were added thereto, and after performing an extraction operation, the organic layer was separated. The aqueous layer was then subject to extraction with ethyl acetate (250 ml), and after washing the combined organic layer with saturated sodium bicarbonate water (250 ml) and saturated saline solution (250 ml) in that order, the organic layer was dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated under a reduced pressure, the concentrate was applied to a silica gel chromatography, and 12.1 g (73%) of the title compound was obtained as a orange syrup from an n-hexane:ethyl acetate=2:1 to 1:2 eluate. The instrumental analysis data for this resulting compound agreed with the data indicated in PCT/JP96/00208.

Workup

  1. additionwas added gradually
  2. temperaturecooling with ice
  3. stirringAfter stirring the reaction solution for 15 minutes at room temperature
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was then subject to extraction with ethyl acetate (250 ml)
  6. washafter washing the combined organic layer with saturated sodium bicarbonate water (250 ml) and saturated saline solution (250 ml) in that order
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. filtrationAfter filtering
  9. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-50d7c4e0771c48d9bce33b29d045dd2b
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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