DL-beta-Phenylalanine → HCID 11833969, compound

HRID 355331Notes

Reaction equation

HRID 355331 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH:5]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.NC(C1C=CC=CC=1)CC(O)=O>>[C:17]1([CH2:16][O:15][C:13]([NH:12][C@H:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:4][C:3]([O:2][CH3:1])=[O:23])=[O:14])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[C:17]1([CH2:16][O:15][C:13]([NH:12][C@@H:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:4][C:3]([O:2][CH3:1])=[O:23])=[O:14])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 69189DL-beta-PhenylalanineHCID 69946905HCID 69946905, compound

Product 2

HCID 11833969HCID 11833969, compoundHCID 71751629Methyl (3S)-3-{[(benzyloxy)carbonyl]amino}-3-phenylpropanoate

Procedure

Methyl-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate (4.87 g), prepared from 3-amino-3-phenylpropionic acid via standard methods, is separated by chiral HPLC [(R,R)-Whelk-O 1 column, elution with 40% isopropyl alcohol in hexane) to give 2.20 g of methyl (S)-β-[[(phenylmethoxy)carbonyl]amino]benzenepropanoate and 2.33 g methyl (R)-β-[[(phenylmethoxy)carbonyl]amino]benzenepropanoate. Each enantiomer is analyzed at >99% ee. Data for (S)-configuration enantiomer

Workup

  1. customis separated by chiral HPLC [
  2. wash(R,R)-Whelk-O 1 column, elution with 40% isopropyl alcohol in hexane)

Sources & evidence

ORD record
ord-3c416f01f6aa4ad4aba447933c6cc44b
Source dataset
uspto-grants-1998_11
Patent number
US05830869

Reaction notes

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