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

HRID 508288Notes

Reaction equation

HRID 508288 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-1d39ae99cff740c6ad94b5cdf27636f8
Source dataset
uspto-grants-2015_08
Patent number
US09095620B2

Reaction notes

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