Tert-butyl 4-{4-[(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)(phenyl)methyl]benzoyl}piperazine-1-carboxylate → N-(cyanomethyl)-4-methyl-2-{phenyl[4-(piperazin-1-ylcarbonyl)phenyl]methoxy}pentanamide

HRID 1180381Notes

Reaction equation

HRID 1180381 reaction equation
[C:1]([CH2:3][NH:4][C:5]([CH:7]([O:12][CH:13]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:14]1[CH:34]=[CH:33][C:17]([C:18]([N:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6])#[N:2]>C(O)=O>[C:1]([CH2:3][NH:4][C:5](=[O:6])[CH:7]([O:12][CH:13]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:14]1[CH:34]=[CH:33][C:17]([C:18]([N:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]2)=[O:19])=[CH:16][CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])#[N:2]

Participants

3

Reactant 1

HCID 86605379Tert-butyl 4-{4-[(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)(phenyl)methyl]benzoyl}piperazine-1-carboxylate

Product 1

HCID 85089179N-(cyanomethyl)-4-methyl-2-{phenyl[4-(piperazin-1-ylcarbonyl)phenyl]methoxy}pentanamide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Tert-butyl 4-{4-[(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)(phenyl)methyl]benzoyl}piperazine-1-carboxylate from step 6 (0.09 g, 0.16 mmol) was dissolved in formic acid (1 mL). The mixture was aged for 2 hours and evaporated under reduced pressure. The crude residue was neutralized using a saturated aqueous solution of NaHCO3. The mixture was extracted 3 times with dichloromethane and the organic layers were dried and evaporated. The crude product was chromatographed on silica gel using 1% NH4OH and 9% methanol in dichloromethane to afford the title compound as a white solid.

Workup

  1. customevaporated under reduced pressure
  2. extractionThe mixture was extracted 3 times with dichloromethane
  3. customthe organic layers were dried
  4. customevaporated
  5. customThe crude product was chromatographed on silica gel using 1% NH4OH and 9% methanol in dichloromethane

Sources & evidence

ORD record
ord-f367ea0ef1c3453198e47b12ed6d4ee1
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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