Trifluoroacetic acid → 1-(2-acetylthiomethyl-5-aminopentanoyl)-L-proline trifluoroacetate

HRID 262816Notes

Reaction equation

HRID 262816 reaction equation
C([O:5][C:6](=[O:36])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:35])[CH:13]([CH2:30][S:31][C:32](=[O:34])[CH3:33])[CH2:14][CH2:15][CH2:16][NH:17]C(OCC1C=CC(OC)=CC=1)=O)(C)(C)C.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>C1(OC)C=CC=CC=1>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[C:32]([S:31][CH2:30][CH:13]([CH2:14][CH2:15][CH2:16][NH2:17])[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:36])=[O:5])=[O:35])(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 228053291-[2-Acetylthiomethyl-5-(p-methoxybenzyloxycarbonylamino)pentanoyl]-L-proline tert-butyl ester

Product 1

HCID 867360071-(2-acetylthiomethyl-5-aminopentanoyl)-L-proline trifluoroacetate

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

1-[2-Acetylthiomethyl-5-(p-methoxybenzyloxycarbonylamino)pentanoyl]-L-proline tert-butyl ester (2 g) is dissolved in a mixture of trifluoroacetic acid (15 ml) and anisole (6 ml). The solution is stored at room temperature for one hour, the solvents are removed in vacuo and the residue is precipitated from ethyl acetate-ether to yield 1-(2-acetylthiomethyl-5-aminopentanoyl)-L-proline trifluoroacetate.

Workup

  1. customthe solvents are removed in vacuo
  2. customthe residue is precipitated from ethyl acetate-ether

Sources & evidence

ORD record
ord-95ad59307b1943bba014927cf6c416d1
Source dataset
uspto-grants-1979_05
Patent number
US04154960

Reaction notes

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