HCID 57609712, compound → HCID 57609723, compound

HRID 416671Notes

Reaction equation

HRID 416671 reaction equation
C([O:8][C:9](=[O:27])[CH2:10][N:11]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])C1C=CC=CC=1>[Pd].C1COCC1>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:11]([CH2:10][C:9]([OH:27])=[O:8])[C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 57609712HCID 57609712, compound

Product 1

HCID 57609723HCID 57609723, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to the representative procedure (Method C) for preparation of keto-acid intermediate from benzyl ester 54e (0.320 mg, 0.866 mmol), palladium on carbon (35 mg) in a mixture of solvent THF (10 mL) afford keto acid 55e (250 mg, 99%) as a colorless oil. IR (neat) 1723, 1612 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.13 (d, J=8.5 Hz, 2H), 6.90 (d, J=8.0 Hz, 2H), 4.51 (s, 2H), 4.05 (s, 2H), 3.81 (s, 3H), 3.68 (s, 2H), 2.30 (s, 3H) (only major peaks were assigned); LRMS (ESI) Calcd. for C14H17NO5 [M−H] 278, found 278; HRMS (ESI) Calcd. for C14H17NO5 [M−H] 278.1028, found 278.1025.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0529a7778f964e65be84086d639ecb69
Source dataset
uspto-grants-2012_01
Patent number
US08088923B2

Reaction notes

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