HCID 59607539, compound → (R)-ethyl 4-(3'-aminobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoate

HRID 1945006Notes

Reaction equation

HRID 1945006 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][C:6]([NH:8][C@H:9]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=2)=[CH:19][CH:18]=1)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:7]>CCO.[Pd]>[NH2:29][C:25]1[CH:24]=[C:23]([C:20]2[CH:19]=[CH:18][C:17]([CH2:16][C@@H:9]([NH:8][C:6](=[O:7])[CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:32])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:22][CH:21]=2)[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 59607539HCID 59607539, compound

Product 1

HCID 59607780(R)-ethyl 4-(3'-aminobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoateYield 91.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of (R)-ethyl 3-(4-methoxy-4-oxobutanamido)-4-(3′-nitrobiphenyl-4-yl)butanoate (123 mg, 0.278 mmol) and Pd/C (59.2 mg, 0.028 mmol) in EtOH (2 ml) is allowed to stir under hydrogen at room temperature for 5.5 hours. The reaction mixture is filtered, and the solution is concentrated to give (R)-ethyl 4-(3′-aminobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoate (105 mg); HPLC retention time=0.84 minutes (condition B); MS (m+1)=413.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.28 (t, J=7.2 Hz, 3H) 2.41-2.65 (m, 6H) 2.85-3.00 (m, 2H) 3.67 (s, 3H) 4.11-4.22 (m, 2H) 4.46-4.54 (m, 1H) 6.31 (br d, J=8.8 Hz, 1H) 6.71-6.74 (m, 1H) 6.95-7.02 (m, 2H) 7.21-7.25 (m, 3H) 7.48-7.50 (m, 2H).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-9d5f1ff04fe245c786239eb4812b77f3
Source dataset
uspto-grants-2013_03
Patent number
US08394853B2

Reaction notes

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