HCID 70431189, compound → HCID 70431208, compound

HRID 2118557Notes

Reaction equation

HRID 2118557 reaction equation
C([O:8][N:9]1[C@@H:12]([CH3:13])[C@H:11]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[C:10]1=[O:25])C1C=CC=CC=1>C1COCC1.[Pd]>[OH:8][N:9]1[C@@H:12]([CH3:13])[C@H:11]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[C:10]1=[O:25]

Participants

4

Reactant 1

HCID 70431189HCID 70431189, compound

Product 1

HCID 70431208HCID 70431208, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The O-benzyl derivative (51) (23.08 g) was taken up in THF (250 ml) and hydrogenolysed in the presence of 10% Pd/C until no starting material remained. The solution was filtered through Kieselguhr and the filtrate evaporated to give a white solid (52) (16.63 g), m.p. 94°-96° C. (from EtoAc--hexane), νmax (KBr) 3400, 1795, 1770, 1720, and 1400 cm-1, δ(CDCl3) 1.45(d, J6.5 Hz, 3H) (irradiation at 4.18 caused this signal to collapse to a s), 4.18 (dq, j6.5 and 2 Hz, 1H), 4.70(d, J2 Hz, 1H) (irradiation at 4.18 caused this signal to collapse to a s), 7.3-8.0 (m, 4H), and 7.7-8.7br (1H, exch.), m/e 246(M+) and 187 (base peak). (Found: C, 58.28; H, 4.11; N, 11.46; M+ 246.0647. C12H10N2O4 requires C, 58.54; H, 4.09; N, 11.38%, M, 246.0681).

Workup

  1. filtrationThe solution was filtered through Kieselguhr
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-1ce7e6d5502f46b3bab6e8cfbbaa5406
Source dataset
uspto-grants-1987_07
Patent number
US04678782

Reaction notes

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