L-Phenylalanine → 1-Phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

HRID 1197788Notes

Reaction equation

[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1C(O)=O.N[C@H](C(O)=O)C[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:13]1([N:1]2[C:2]3=[N:1][CH:2]=[CH:3][CH:4]=[C:3]3[CH2:4][C:5]2=[O:6])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Reactant 2

HCID 6140L-Phenylalanine

HCID 7405L-Pyroglutamic Acid

Product 1

HCID 149872061-Phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-oneYield 55%

Procedure

The compound was prepared as described by Ting, Kaminski, et al., in "Substituted 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-ones as Potential Antiinflammatory Agents", J. Med. Chem., 1990, 33, 2697-2706 in 55% yield; mp 116.0°-117.0° C.; IR(KBr): 1727 cm-1 (CO); 1H NMR(CDCl3TMS): d 3.73 (s, 2H, CH2 --CO), [7.00 (dd, 1H), 7.39 (dd, 1H), 8.18 (d, 1H), 2,3-subs. Pyr], 7.51 (m, 5H, Phe); mass spec m/e 211 (M+1); Anal calcd for C13H10N2O, MW 210.24: C, 74.27; H, 4.79; N, 13.33. Found: C, 74.11; 4.73; N, 12.92.

Workup

customThe compound was prepared

Sources & evidence

ORD record: ord-8cf37738fdc440589c5d8324538a154f
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05278162

Reaction notes

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