Sulfuric Acid → (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate

HRID 1021040Notes

Reaction equation

HRID 1021040 reaction equation
[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]2[N:12](C(=O)C(C)(C)C)[C:11](=[O:19])[C@H:10]([CH3:20])[CH2:9]2)=[CH:3][CH:2]=1.S(=O)(=O)(O)O>C(O)C>[CH2:11]([O:19][C:11](=[O:19])[C@H:10]([CH3:20])[CH2:9][C@H:8]([NH2:12])[CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:6][CH:5]=1)[CH3:10]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 66738857(3R,5S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3-methylpyrrolidin-2-one

Product 1

HCID 25017087(2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g (3R,5S)-5-biphenyl-4-ylmethyl-3-methylpyrrolidin-2-one (2-a, R1=H), 10 ml ethanol and 0.4 ml concentrated sulphuric acid were heated at about 80-120° C. for about 24 hours. The mixture was evaporated to dryness to obtain (2R,4S)-4-amino-5-biphenyl-4-yl-2-methylpentanoic acid ethyl ester (hydrogen sulphate salt). Spectroscopic data as in Example 44.

Workup

  1. customThe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-12b36d89a0ee4f31aaf144587e2df2e9
Source dataset
uspto-grants-2014_05
Patent number
US08716495B2

Reaction notes

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