Acetonitrile → Trifluoroacetic acid

HRID 895708Notes

Reaction equation

HRID 895708 reaction equation
[NH2:1][CH:2]([CH2:6][CH2:7][C:8](=[O:31])[NH:9][CH:10]([C:24](=[O:30])[NH:25][CH2:26][C:27]([OH:29])=[O:28])[CH2:11][S:12][CH2:13][C:14](=O)[C:15](=[O:22])[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:3]([OH:5])=[O:4].[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33].[NH2:39][OH:40].Cl.C(#N)C>O>[NH2:1][CH:2]([CH2:6][CH2:7][C:8](=[O:31])[NH:9][CH:10]([C:24](=[O:30])[NH:25][CH2:26][C:27]([OH:29])=[O:28])[CH2:11][S:12][CH2:13][C:14](=[N:39][OH:40])[C:15](=[O:22])[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:3]([OH:5])=[O:4].[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 443297Hydroxyamine hydrochloride2×HCID 10226480HCID 10226480, compound

Product 2

HCID 6422Trifluoroacetic acidYield 95.1%HCID 86587154HCID 86587154, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2-Amino-4-[1-(carboxymethyl-carbamoyl)-2-(2,3-dioxo-3-piperidin-1-yl-propylsulfanyl)-ethylcarbamoyl]-butyric acid as its TFA salt (400 mg, 0.696 mol) was dissolved in 8 mL of water to which was added 1.3 eq. of solid NH2OH.HCl at 0° C. and the homogeneous solution was left standing over-night. LC/MS indicated that the reaction was incomplete. An additional 1 eq. of NH2OH.HCl was added at room temperature and the homogeneous solution was left standing overnight. LC/MS indicated complete conversion of the starting amide to the corresponding oxime. The aqueous mixture was then passed through reversed-phase C18 column using water and acetonitrile mixture as gradient eluent. The pure fractions were pooled, concentrated under vacuum at room temperature to one fourth of the volume and finally freeze-dried to obtain 2-amino-4-[1-(carboxymethyl-carbamoyl)-2-(2-hydroxyimino-3-oxo-3-piperidin-1-yl-propylsulfanyl)-ethylcarbamoyl]-butyric acid as its TFA salt (390 mg, 95.1%).

Workup

  1. waitthe homogeneous solution was left
  2. waitstanding over-night
  3. waitthe homogeneous solution was left
  4. concentrationconcentrated under vacuum at room temperature to one fourth of the volume
  5. customfinally freeze-dried

Sources & evidence

ORD record
ord-cada59a5805449c1823a6615f28d8be9
Source dataset
uspto-grants-2005_07
Patent number
US06916850B2

Reaction notes

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