Ethanol → HCID 54400622, compound

HRID 487473Notes

Reaction equation

HRID 487473 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([NH:28]C=O)[CH:6]=[C:7]([CH:19]1[CH2:24][CH2:23][N:22]([C:25](=[O:27])[CH3:26])[CH2:21][CH2:20]1)[CH2:8][P:9]([O:15]C(C)C)([O:11]C(C)C)=[O:10])[CH3:2].C(O)C>ClCCl>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([NH2:28])[CH:6]=[C:7]([CH:19]1[CH2:20][CH2:21][N:22]([C:25](=[O:27])[CH3:26])[CH2:23][CH2:24]1)[CH2:8][P:9]([OH:15])([OH:11])=[O:10])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 54097399HCID 54097399, compound

Product 1

HCID 54400622HCID 54400622, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.15 g (6.84 mmol) of 4-(1-acetylpiperidin-4-yl)-5-diisopropylphosphono-2-formylamino-pent-3-enoic acid ethyl ester are dissolved in 17 ml of dichloromethane, and 3.54 ml (27.3 mmol) of trimethylbromossilane are added dropwise at room temperature. The mixture is left to stand room at temperature for 16 hours, 17 ml of ethanol are added dropwise, the mixture is left to stand for a further 18 hours and is concentrated by evaporation in a rotary evaporator, the residue is dissolved in 12 ml of ethanol, and a mixture of 3 ml of propylene oxide and 3 ml of ethanol is added. A suspension forms, which is stirred for a further 2 hours at room temperature and for 2 hours with ice cooling and is then filtered with suction. 2-amino-4-(1-acetylpiperidin-4-yl)-5-phosphono-pent-3-enoic acid ethyl ester having a melting point of 225° (decomp.) is obtained.

Workup

  1. addition3.54 ml (27.3 mmol) of trimethylbromossilane are added dropwise at room temperature
  2. waitThe mixture is left
  3. customfor 16 hours
  4. waitthe mixture is left
  5. concentrationis concentrated by evaporation in a rotary evaporator
  6. dissolutionthe residue is dissolved in 12 ml of ethanol
  7. additiona mixture of 3 ml of propylene oxide and 3 ml of ethanol
  8. additionis added
  9. filtrationis then filtered with suction

Sources & evidence

ORD record
ord-cdab242882fb4fcea0fdcc012ab4cfa8
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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