HOAt → HCID 66811536, compound

HRID 1099205Notes

Reaction equation

HRID 1099205 reaction equation
[NH:1]([C:3]([CH:5]1[CH2:8][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:6]1)=[O:4])[NH2:2].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]1[C:38](O)=[O:39])=[O:25])([CH3:22])([CH3:21])[CH3:20].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.S([O-])(O)(=O)=O.[K+]>CN(C=O)C.O.CCOC(C)=O>[CH2:12]([O:11][C:9]([N:7]1[CH2:8][CH:5]([C:3]([NH:1][NH:2][C:38]([CH:27]2[CH:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:29][CH2:30][CH2:31][N:26]2[C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])=[O:39])=[O:4])[CH2:6]1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 181649HOAtHCID 516920Potassium bisulfateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 450739411-(tert-Butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acidHCID 56923840HCID 56923840, compound

Product 1

HCID 66811536HCID 66811536, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 3-(hydrazinocarbonyl)azetidine-1-carboxylate (350 mg, 1.40 mmol) in DMF (10 ml) were added 1-(tert-butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid (1A.5, 427 mg, 1.40 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (322 mg, 1.68 mmol), and 1-hydroxy-7-azabenzotriazole (95.3 mg, 0.700 mmol). The reaction was allowed to stir for 48 h, and then poured onto 10% potassium hydrogen sulfate and diluted with water (10 ml) and EtOAc (30 ml). The organic portion was isolated, washed with 3M lithium chloride (2×) and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified via flash chromatography (silica, 0-50% EtOAc/hexanes) to yield tert-butyl 2-{[2-({1-[(benzyloxy)carbonyl]azetidin-3-yl}carbonyl)hydrazino]carbonyl}-3-phenylpiperidine-1-carboxylate (31%).

Workup

  1. customThe organic portion was isolated
  2. washwashed with 3M lithium chloride (2×) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified via flash chromatography (silica, 0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-91a4af5f4fe847cf99f9fc059d5b9b6c
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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