(R)-tert-butyl 3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoate → (R)-3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoic acid

HRID 881856Notes

Reaction equation

HRID 881856 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:18])[CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])=[CH:3][CH:2]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@@H:8]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:18])[CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 59607897(R)-tert-butyl 3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoate

Product 1

HCID 59607696(R)-3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoic acidYield 96.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (R)-tert-butyl 3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoate (40 mg, 0.094 mmol) in DCM (0.5 mL), TFA (0.15 mL) is added at room temperature. The mixture is allowed to stir for 2 hours, and then concentrated under reduced pressure to give (R)-3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoic acid (33.5 mg, 96%). HPLC retention time=1.20 minutes (condition A); MS (m+1)=370.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.21-2.29 (m, 1 H) 2.38-2.45 (m, 1 H) 2.62-2.66 (m, 1 H) 2.75-3.00 (m, 4 H) 3.29-3.37 (m, 1 H) 3.45-3.53 (m, 4 H) 6.12 (br s, 1 H) 7.23 (d, J=8 Hz, 2 H) 7.32-7.35 (m, 1 H) 7.41-7.45 (m, 2 H) 7.53 (d, J=8.1 Hz, 2 H) 7.56-7.59 (m, 2 H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c894b49b4c1c486d8d84074c0750e229
Source dataset
uspto-grants-2015_03
Patent number
US08993631B2

Reaction notes

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