Hydrazine hydrate (1:1) → HCID 178452607, compound

HRID 132114Notes

Reaction equation

HRID 132114 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:11]2([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:16][CH2:15][C:14](=O)/[C:13](=[CH:18]/[N:19](C)C)/[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.[NH2:31]N>C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:11]2([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:16][CH2:15][C:14]3[C:13](=[CH:18][NH:19][N:31]=3)[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59733753HCID 59733753, compound

Product 1

HCID 178452607HCID 178452607, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (E)-tert-butyl 1-(3-tert-butylphenyl)-3-((dimethylamino) methylene)-4-oxocyclohexylcarbamate (801 mg, 2.0 mmol) in 6 mL of ethanol was added hydrazine monohydrate (150 μL, 3.0 mmol). The reaction was allowed to stir for 3 h. The reaction was concentrated and purified using a biotage 40S column eluting with DCM/MeOH (95:5) to afford 500 mg (67% yield) of an off white foam. LCMS corresponded to the desired material: retention time (min)=2.45 (method [8]); MS (ESI) 370.0.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified
  3. washeluting with DCM/MeOH (95:5)
  4. customto afford 500 mg (67% yield) of an off white foam

Sources & evidence

ORD record
ord-5d156b123a704ec2950679246dfacef0
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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