HCID 23446387, compound → HCID 23446388, compound

HRID 1265492Notes

Reaction equation

HRID 1265492 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][C:15]([NH:17][C:18]3[CH:19]=[C:20]([C:24]([O-:26])=[O:25])[N:21]([CH3:23])[CH:22]=3)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>C1COCC1.[Pd]>[CH:10]1[C:11]2[CH:12]([CH2:14][C:15]([NH:17][C:18]3[CH:19]=[C:20]([C:24]([OH:26])=[O:25])[N:21]([CH3:23])[CH:22]=3)=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 23446387HCID 23446387, compound

Product 1

HCID 23446388HCID 23446388, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the benzylester (20a) (900 mg) dissolved in THF (10 ml) was added 10% Pd/C (100 mg). The solution was hydrogenated (1 atm) for 19 hours and worked up using standard methods to yield 580 mg (80%) of compound (21a). 1H NMR (DMSO-d6) δ9.4 (s, 1 H), 8.0 (m, 2 H), 7.8 (m, 2 H), 7.3 (m, 4 H), 7.1 (s, 1 H), 6.8 (s, 1 H), 4.6 (m, 2 H), 4.3 (m, 1 H), 3.8 (s, 3 H).

Workup

  1. customfor 19 hours

Sources & evidence

ORD record
ord-dbd6c83731314e7aba3181215751b1bd
Source dataset
uspto-grants-2003_04
Patent number
US06545162B1

Reaction notes

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