Methanol → N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

HRID 2260416Notes

Reaction equation

HRID 2260416 reaction equation
[CH:1]([NH:3][C@@H:4]1[C:9](=[O:10])[O:8][C:6](=[O:7])[CH2:5]1)=[O:2].[NH2:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CO>O>[CH:1]([NH:3][C@H:4]([C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[CH2:5][C:6](=[O:7])[OH:8])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6140L-PhenylalanineHCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

Product 1

HCID 92472N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The preparation of N-formyl-L-aspartic anhydride was repeated several times in order to prepare multiple first reaction mixtures. To each of these first reaction mixtures was added 100 ml of one of the alkyl ester or hindered alcohol solvents listed in Table 1 followed by the addition of 44.6 grams (0.27 mole) of L-phenylalanine. The resulting slurries were maintained at room temperature for 5 hours for completion of the in situ coupling process. As the reaction proceeded, the slurries became more and more solidified in each reaction and a quantity of a methanol and water solution (10:1) was added in order to dissolve all the solids therein. 2.0 grams aliquots were analyzed in each reaction mixture by HPLC. The resulting α/β ratios of N-formyl-L-aspartyl-L-phenylalanine formed in each reaction are as follows:

Workup

  1. customto prepare multiple
  2. customfirst reaction mixtures
  3. customTo each of these first reaction mixtures
  4. customthe slurries became more and more solidified in each reaction
  5. dissolutionto dissolve all the solids

Sources & evidence

ORD record
ord-6b80c21a8e934dabb858a3d3d717bb88
Source dataset
uspto-grants-1995_12
Patent number
US05476961

Reaction notes

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