Methanol → N-benzoyl-D-phenylalanine

HRID 223790Notes

Reaction equation

HRID 223790 reaction equation
[C:1]([NH:9][C:10](=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].CO>C(O)C>[C:1]([NH:9][C@@H:10]([C:11]([OH:13])=[O:12])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2230353-Phenyl-2-(phenylformamido)prop-2-enoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 721472N-benzoyl-D-phenylalanineYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.2 grams of α-benzamido-cinnamic acid were dissolved in 40 ml of absolute ethanol and treated with 0.3 ml of the catalyst solution produced in Example 19. The reaction mixture was sucked into a 100 ml autoclave. It was pressurized with 6 bars of hydrogen pressure. After taking up the theoretical amount of hydrogen it was worked up as customary (e.g. see Example 6). There were isolated 3.15 grams of N-benzoyl-(R)-phenylalanine having the rotary value of [α]D27 =+38.6° (c=1/CH3OH), corresponding to an optical yield of 95.8%.

Sources & evidence

ORD record
ord-0bc304e9bf4545c7bca10e87c141041d
Source dataset
uspto-grants-1982_10
Patent number
US04356324

Reaction notes

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