Hydrochloric Acid → HCID 86756441, compound

HRID 636026Notes

Reaction equation

HRID 636026 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:28])[C@@H:8]([NH:20]C(OC(C)(C)C)=O)[C@H:9]([CH3:19])[CH2:10][CH2:11][NH:12][CH2:13][N:14]=[N:15][N+:16]([O-:18])=[O:17].[ClH:29]>C1COCC1.O1CCOCC1>[ClH:29].[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:28])[C@@H:8]([NH2:20])[C@H:9]([CH3:19])[CH2:10][CH2:11][NH:12][CH2:13][N:14]=[N:15][N+:16]([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86756440HCID 86756440, compound

Product 1

HCID 86756441HCID 86756441, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

(2S,3R)-2-tert-Butoxycarbonylamino-3-methyl-5-(nitroimino-amino)methylaminopentanoic acid 1,3-thiazol-2-ylamide (101 mg, 0.243 mmol) is dissolved in 1 mL THF and 1.5 mL of 4 N HCl in dioxane is added. After 2 h, THF is added and the white precipitate is collected by filtration. The resulting oily solid is treated with methanol and concentrated in vacuo. THF is added and the mixture is concentrated in vacuo; this THF addition and concentration is repeated several times to give (2S,3R)-2-amino-3-methyl-5-(nitroimino-amino)methylaminopentanoic acid 1,3-thiazol-2-ylamide hydrochloride as a solid (83 mmol, 97%).

Workup

  1. filtrationthe white precipitate is collected by filtration
  2. additionThe resulting oily solid is treated with methanol
  3. concentrationconcentrated in vacuo
  4. additionTHF is added
  5. concentrationthe mixture is concentrated in vacuo
  6. additionthis THF addition and concentration

Sources & evidence

ORD record
ord-be0b70b8cc2349ceb560d4e18e8892ed
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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