Methyl 4-oxobutyrate → 1-Benzhydrylamino-3-carbomethoxypropanephosphonous acid

HRID 25984

Reaction equation

HRID 25984 reaction equation
[C:1]([CH2:5][CH2:6][CH:7]=O)([O:3][CH3:4])=[O:2].[Na].[PH2:10]([O-:12])=[O:11].[CH:13]([NH3+:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH:13]([NH:26][CH:7]([P:10]([OH:12])[OH:11])[CH2:6][CH2:5][C:1]([O:3][CH3:4])=[O:2])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 83779Methyl 4-oxobutyrateHCID 5360545Sodium2×HCID 178527021HCID 178527021, compound

Product 1

HCID 213258971-Benzhydrylamino-3-carbomethoxypropanephosphonous acid

Procedure

5.8 parts of freshly distilled 3-carbomethoxypropionaldehyde in 10 parts of sodium-dried dioxan was added to a suspension of 12.4 parts benzhydrylammonium hypophosphite in 60 parts of sodium-dried dioxan at 100° and under nitrogen over 15 minutes. 40 Parts water/dioxan was removed by distillation during the addition such that the temperature remained at 100° or above. The resulting clear solution was cooled and diluted with an equal volume of alcohol to give DL-1-benzhydrylamino-3-carbomethoxypropanephosphonous acid, melting point 162°-164°.

Workup

  1. custom40 Parts water/dioxan was removed by distillation during the addition such that the temperature
  2. customremained at 100° or above
  3. temperatureThe resulting clear solution was cooled
  4. additiondiluted with an equal volume of alcohol

Sources & evidence

ORD record
ord-f07ea71693684b45bf4ee60818f6711a
Source dataset
uspto-grants-1979_04
Patent number
US04147780

Linked notes

Loading…