Trifluoroacetic acid → (2S,3R)-2-amino-3-tert-butoxy-N-(1-pyrimidin-2-yl-cyclopropyl)-butyramide trifluoro-acetic acid

HRID 1040500Notes

Reaction equation

HRID 1040500 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:16](=[O:27])[NH:17][C:18]1([C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:20][CH2:19]1)[C@H:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:10])(C)(C)C.[C:29]([OH:35])([C:31]([F:34])([F:33])[F:32])=[O:30]>C(Cl)Cl>[F:32][C:31]([F:34])([F:33])[C:29]([OH:35])=[O:30].[NH2:7][C@@H:8]([C@H:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH3:10])[C:16]([NH:17][C:18]1([C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:19][CH2:20]1)=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67390977[(1S,2R)-2-tert-butoxy-1-(1-pyrimidin-2-yl-cyclopropylcarbamoyl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 67389830(2S,3R)-2-amino-3-tert-butoxy-N-(1-pyrimidin-2-yl-cyclopropyl)-butyramide trifluoro-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(1S,2R)-2-tert-butoxy-1-(1-pyrimidin-2-yl-cyclopropylcarbamoyl)-propyl]-carbamic acid tert-butyl ester (0.17 g, 0.45 mmol) was dissolved in DCM (1 mL) and to this was added TFA (0.2 mL). The reaction was allowed to stir at RT for 24 h. The solvent was removed under reduced pressure and the residue triturated with Et2O to give (2S,3R)-2-amino-3-tert-butoxy-N-(1-pyrimidin-2-yl-cyclopropyl)-butyramide trifluoro-acetic acid (0.16 g, 0.45 mmol) as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue triturated with Et2O

Sources & evidence

ORD record
ord-ff001e8bbfca4171a3d9c63355f09863
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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