Hydrochloric Acid → HCID 86591641, compound

HRID 600890Notes

Reaction equation

HRID 600890 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]([OH:12])=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:25]1([C@@H:31]([NH:33][CH2:34][C:35]([C:37]2([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:39][CH2:38]2)=[O:36])[CH3:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>O1CCCC1.C(OCC)(=O)C>[CH2:7]([O:6][P:4]([CH2:9][C:10]([N:33]([CH2:34][C:35]([C:37]1([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:38][CH2:39]1)=[O:36])[C@H:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:32])=[O:12])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 36704(Diethoxyphosphinyl)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 11346406HCID 11346406, compound

Product 1

HCID 86591641HCID 86591641, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Diethylphosphonoacetic acid (15.1 g, 76.8 mmol) was dissolved in anhydrous tetrahydrofuran (120 ml), and after adding 1,1′-carbonyldiimidazole (13.7 g, 84.5 mmol) while cooling with ice, it was stirred at room temperature for 1 hour. After adding an anhydrous tetrahydrofuran (30 ml) solution of ethyl 1-[2-[N-[1-(S)-phenylethyl]amino]acetyl]cyclopropanecarboxylate (17.6 g, 64.0 mmol) to the reaction solution while cooling with ice, it was stirred at room temperature for 1 hour. After adding 1 mol/l hydrochloric acid (100 ml) and ethyl acetate (100 ml) to the reaction solution and performing an extraction operation, the organic layer was separated. The aqueous layer was then subjected to extraction with ethyl acetate (100 ml) and the combined organic layer was washed with saturated sodium bicarbonate water (100 ml) and saturated saline solution (100 ml) in that order, and then dried over anhydrous sodium sulfate. After filtering and then concentrating the filtrate under a reduced pressure, 28.7 g (99%) of the title compound was obtained as a yellow syrup.

Workup

  1. temperaturewhile cooling with ice, it
  2. temperaturewhile cooling with ice, it
  3. stirringwas stirred at room temperature for 1 hour
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was then subjected to extraction with ethyl acetate (100 ml)
  6. washthe combined organic layer was washed with saturated sodium bicarbonate water (100 ml) and saturated saline solution (100 ml) in that order
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtering
  9. concentrationconcentrating the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-2683862fdb9447418341d53c8f358f9e
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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