Trifluoroacetic acid → 3-Amino-propionic acid dipropylcarbamoylmethyl ester trifluoroacetate

HRID 386703Notes

Reaction equation

HRID 386703 reaction equation
[CH2:1]([N:4]([CH2:24][CH2:25][CH3:26])[C:5]([CH2:7][O:8][C:9](=[O:23])[CH2:10][CH2:11][NH:12]C(OCC1C=CC=CC=1)=O)=[O:6])[CH2:2][CH3:3].C(OC(C)C)(=O)C.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>[Pd]>[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[CH2:24]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([CH2:7][O:8][C:9](=[O:23])[CH2:10][CH2:11][NH2:12])=[O:6])[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7915Isopropyl AcetateHCID 667979022-(Dipropylamino)-2-oxoethyl 3-(((benzyloxy)carbonyl)amino)propanoate

Product 1

HCID 866633463-Amino-propionic acid dipropylcarbamoylmethyl ester trifluoroacetate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
20 °C

Procedure

A solution of 3-benzyloxycarbonylamino-propionic acid dipropylcarbamoylmethyl ester in isopropyl acetate (33.2 g, 91.0 mmol in 129.9 g total mass of solution) was treated with TFA (7.05 ml, 92.0 mmol) while the internal temperature was maintained at 20° C., followed by 10% Pd/C (3.3 g, 50% wet) and stirred under an atmosphere of H2 (3 atm) for 3.5 h to afford 3-amino-propionic acid dipropylcarbamoylmethyl ester trifluoroacetate.

Sources & evidence

ORD record
ord-7f00752dff8a47c89866a3cda0794182
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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