1-[3-(acetylthio)-2-tert-butoxycarbonylaminomethylpropanoyl]-L-proline tert-butyl ester → 1-(3-acetylthio-2-aminomethylpropanoyl)-L-proline

HRID 262827Notes

Reaction equation

HRID 262827 reaction equation
C([O:5][C:6](=[O:29])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:28])[CH:13]([CH2:19][NH:20]C(OC(C)(C)C)=O)[CH2:14][S:15][C:16](=[O:18])[CH3:17])(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[C:16]([S:15][CH2:14][CH:13]([CH2:19][NH2:20])[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:29])=[O:5])=[O:28])(=[O:18])[CH3:17]

Participants

4

Reactant 1

HCID 228053301-[3-(acetylthio)-2-tert-butoxycarbonylaminomethylpropanoyl]-L-proline tert-butyl ester

Product 1

HCID 537828151-(3-acetylthio-2-aminomethylpropanoyl)-L-proline

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

1-[3-(acetylthio)-2-tert-butyloxycarbonylaminomethylpropanoyl]-L-proline tert-butyl ester (1.5 g) is dissolved in a mixture of anisole (6 ml) and trifluoroacetic acid (12 ml) and the solution is stored at room temperature for one hour. The solvent is removed in vacuo, the residue is distributed between water and ether. The aqueous phase is washed twice with ether and freeze-dried to yield 1-(3-acetylthio-2-aminomethylpropanoyl)-L-proline.

Workup

  1. customThe solvent is removed in vacuo
  2. washThe aqueous phase is washed twice with ether
  3. customfreeze-dried

Sources & evidence

ORD record
ord-72b4b9c25a6d4b4594c70a1be8c0008f
Source dataset
uspto-grants-1979_05
Patent number
US04154960

Reaction notes

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