Methanol → HCID 53998134, compound

HRID 1740538Notes

Reaction equation

HRID 1740538 reaction equation
[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][CH:18]=O)=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].B.CSC.CO>O1CCCC1>[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][CH3:18])=[CH:15][CH:16]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 12423031(Dimethyl sulfide)trihydroboronHCID 57173967HCID 57173967, compound

Product 1

HCID 53998134HCID 53998134, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 100.0 g of methyl (2S)-2-ethanamido-3-(4-methanamidophenyl)propanoate in 3000 cm3 of tetrahydrofuran at 20° C. with stirring are added, under nitrogen, 378 cm3 of a 2 M solution of borane/methyl sulphide in tetrahydrofuran such that the temperature of the reaction mixture is maintained below 25° C. At the end of the addition, the reaction mixture is kept stirring for 1 hour at 25° C. and 1000 cm3 of methanol are then added dropwise. At the end of the addition of the methanol, the mixture is stirred at 25° C. under nitrogen for 16 hours and then concentrated under reduced pressure (20 kPa) at a temperature of 40° C. At the end of the concentration, the mixture is allowed to return to 25° C. under nitrogen and 1000 cm3 of dichloromethane and 1000 cm3 of saturated aqueous sodium chloride solution are then added. The mixture is stirred for 30 minutes at 25° C. and is then separated by settling of the phases. The lower organic phase is removed and dried over anhydrous sodium sulphate. After filtration of the sodium sulphate, the solution is concentrated at 30° C. under reduced pressure (20 kPa).

Workup

  1. additionare added, under nitrogen
  2. additionAt the end of the addition
  3. stirringthe mixture is stirred at 25° C. under nitrogen for 16 hours
  4. concentrationconcentrated under reduced pressure (20 kPa) at a temperature of 40° C
  5. concentrationAt the end of the concentration
  6. customto return to 25° C. under nitrogen
  7. addition1000 cm3 of dichloromethane and 1000 cm3 of saturated aqueous sodium chloride solution are then added
  8. stirringThe mixture is stirred for 30 minutes at 25° C.
  9. customis then separated
  10. customThe lower organic phase is removed
  11. dry with materialdried over anhydrous sodium sulphate
  12. filtrationAfter filtration of the sodium sulphate
  13. concentrationthe solution is concentrated at 30° C. under reduced pressure (20 kPa)

Sources & evidence

ORD record
ord-46ada9c1e8794abc8979fd525e433710
Source dataset
uspto-grants-1999_10
Patent number
US05969179

Reaction notes

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