Hydrochloric Acid → 3-Amino-4-phenyl-1-[N-(4-pyridin-2-yl-benzyl)-hydrazino]-butan-2-ol trihydrochloride

HRID 1909353Notes

Reaction equation

HRID 1909353 reaction equation
C(OC([NH:8][N:9]([CH2:23][CH:24]([OH:41])[CH:25]([NH:33]C(OC(C)(C)C)=O)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:13][CH:12]=1)=O)(C)(C)C.[ClH:42]>O1CCOCC1>[ClH:42].[ClH:42].[ClH:42].[NH2:33][CH:25]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH:24]([OH:41])[CH2:23][N:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:13][CH:12]=1)[NH2:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10940720N'-(3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-N'-(4-pyridin-2-yl-benzyl)-hydrazinecarboxylic acid tert-butyl ester

Product 1

HCID 183691273-Amino-4-phenyl-1-[N-(4-pyridin-2-yl-benzyl)-hydrazino]-butan-2-ol trihydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The Boc-aza-isostere (7) (1.2 g, 2.1 mmol) was taken up in 1,4-dioxane (16 mL), and stirred at room temperature, under nitrogen. After five minutes, 4N HCl (12 mL) was added via syringe. There was immediate precipitate formation, and the mixture was stirred at room temperature, under nitrogen. After approximately 18 hours, the dioxane was removed under reduced pressure. The yellow residue was azeotroped with toluene (3×25 mL), and then dried under high vacuum. After 6 hours under high vacuum, 0.92 g (91%) of (8) was obtained as a yellow solid. 1H NMR (CD3OD) δ 8.87 (d, 1H), 8.69 (m, 1H), 8.42 (d, 1H), 8.06 (m, 3H), 7.80 (d, 2H), 7.28 (m, 6H), 4.25 (m, 3H), 3.13 (m, 2H), 2.88 (d, 2H); MS (M)+=472.

Workup

  1. stirringthe mixture was stirred at room temperature, under nitrogen
  2. waitAfter approximately 18 hours
  3. customthe dioxane was removed under reduced pressure
  4. customThe yellow residue was azeotroped with toluene (3×25 mL)
  5. customdried under high vacuum
  6. waitAfter 6 hours under high vacuum

Sources & evidence

ORD record
ord-8e03bda410ec4a4d93b72bda3d8eb362
Source dataset
uspto-grants-2013_12
Patent number
US08598364B2

Reaction notes

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