Nitric Acid → HCID 178473866, compound

HRID 1271526Notes

Reaction equation

HRID 1271526 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[C:17]([NH:19][C@H:20]([C:28]([C:30]1[S:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1)=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:27])[NH2:26])=[O:18])(=[O:10])[CH3:9].[N+:39]([O-:42])([OH:41])=[O:40]>C(#N)C>[N+:39]([O-:42])([OH:41])=[O:40].[C:8]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[C:17]([NH:19][C@H:20]([C:28]([C:30]1[S:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1)=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:26])[NH2:27])=[O:18])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 178473864HCID 178473864, compound

Product 1

HCID 178473866HCID 178473866, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of the TFA salt of the single diastereomer (2S,4R)-1-acetyl-N-[(1S)-1-(2-benzothiazolylcarbonyl)-4-[[imino(amino)methyl]amino]butyl]-4-hydroxypyrrolidine-2-carboxamide (0.30 g, 0.493 mmol) in acetonitrile (4 mL) was added the solution of nitric acid (43.7 mg, 0.493 mmol) in acetonitrile (1 mL). A suspension formed upon mixing. The suspension was heated to partially dissolve the solid and then cooled to precipitate the title compound as a solid. The solid nitrate salt was filtered and dried in a vacuum oven at 30° C.

Workup

  1. customA suspension formed
  2. additionupon mixing
  3. temperatureThe suspension was heated
  4. dissolutionto partially dissolve the solid
  5. temperaturecooled
  6. customto precipitate the title compound as a solid
  7. filtrationThe solid nitrate salt was filtered
  8. customdried in a vacuum oven at 30° C.

Sources & evidence

ORD record
ord-0317007d67564b43a37947eeffa2847e
Source dataset
uspto-grants-2007_04
Patent number
US07205384B2

Reaction notes

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