Nitrogen → Nalpha-Acetyl-p-Nitro-D-Phenylalanine Methyl Ester

HRID 280043

Reaction equation

HRID 280043 reaction equation
[C:1]([NH:4][C@@H:5]([C:16]([OH:18])=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[N+](=[CH2:21])=[N-].N(CNC(N)=O)=O.[OH-].[K+].N#N>O1CCCC1.CCOCC>[CH3:21][O:17][C:16](=[O:18])[C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)[NH:4][C:1](=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 947NitrogenHCID 9550Diazomethane3×HCID 14797Potassium HydroxideHCID 104823Urea, (nitrosomethyl)-HCID 7039504(R)-2-Acetamido-3-(4-nitrophenyl)propanoic acid

Product 1

HCID 10978383Nalpha-Acetyl-p-Nitro-D-Phenylalanine Methyl Ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 7 was dissolved in tetrahydrofuran (120 ml) and cooled in an ice bath. Diazomethane was generated by addition of N-nitrosomethylurea to an ice cold, equivolume mixture of ether and 40% aqueous potassium hydroxide. The diazomethane solution was added without purification to the stirred solution of the amino acid derivative. The reaction was complete when N2 was no longer evolved upon addition of diazomethane. Excess diazomethane was consumed by the addition of acetic acid. The solution was extracted successively with saturated saline, 1M sodium bicarbonate, 0.1M HCl, and again with saline and dried (MgSO4). Evaporation left 3.56 g (88.4%) of a solid melting at 110°-112° C. which was pure by TLC (chloroform/methanol acid: 85/10/5). [α]D25 =-13.8 (c=2.1, ethanol)

Workup

  1. temperaturecooled in an ice bath
  2. customExcess diazomethane was consumed by the addition of acetic acid
  3. extractionThe solution was extracted successively with saturated saline, 1M sodium bicarbonate, 0.1M HCl
  4. dry with materialagain with saline and dried (MgSO4)
  5. customEvaporation
  6. waitleft 3.56 g (88.4%) of a solid melting at 110°-112° C. which

Sources & evidence

ORD record
ord-c6a4f985272e48bab99db4486b2e89fc
Source dataset
uspto-grants-1986_05
Patent number
US04587046

Linked notes

Loading…