Nitric Acid → HCID 178473867, compound

HRID 1271528Notes

Reaction equation

HRID 1271528 reaction equation
[C:1]([N:4]1[CH2:8][C@H:7]([OH:9])[CH2:6][C@H:5]1[C:10]([NH:12][C@H:13]([C:21]([C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1)=[O:22])[CH2:14][CH2:15][CH2:16][NH:17][CH:18]=[N:19][NH2:20])=[O:11])(=[O:3])[CH3:2].[N+:32]([O-:35])([OH:34])=[O:33]>C(#N)C.C(O)C>[N+:32]([O-:35])([OH:34])=[O:33].[C:1]([N:4]1[CH2:8][C@H:7]([OH:9])[CH2:6][C@H:5]1[C:10]([NH:12][C@H:13]([C:21]([C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1)=[O:22])[CH2:14][CH2:15][CH2:16][NH:17][CH:18]=[N:19][NH2:20])=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 178473865HCID 178473865, compound

Product 1

HCID 178473867HCID 178473867, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent3×

Procedure

(2S,4R)-1-Acetyl-N-[(1S)-4-[(aminoiminomethyl)amino]-1-(2-benzothiazolylcarbonyl)butyl]-4-hydroxy-2-pyrrolidinecarboxamide as a free base in a diastereomeric ratio of 40:60 (591 mg, 1.27 mmol) was dissolved into a mixture of acetonitrile (6 mL) and ethanol (8 mL). To the mixture was added a solution of nitric acid (113 mg, 1.27 mmol) in acetonitrile (2 mL). Additional acetonitrile was then added until the cloud point. To the mixture were then added seeds of the desired nitrate salt. (The seeds were prepared by reacting chromatographed single diastereomer of the corresponding TFA salt with nitric acid, as described in Example 10). The mixture was then stirred for 18 hours at ambient temperature. The solid was filtered, washed with acetonitrile and dried in a vacuum oven to yield the title compound as an off-white solid.

Workup

  1. custom(The seeds were prepared
  2. customby reacting chromatographed single diastereomer of the corresponding TFA salt with nitric acid
  3. filtrationThe solid was filtered
  4. washwashed with acetonitrile
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-7d4685efc2e246a3bd662175b5658eae
Source dataset
uspto-grants-2007_04
Patent number
US07205384B2

Reaction notes

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