1,2-Dichloroethane → HCID 131731738, compound

HRID 2402430Notes

Reaction equation

HRID 2402430 reaction equation
O[NH:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1.[C:22]([O:26][C:27]([NH:29][C:30]1([C:33](O)=[O:34])[CH2:32][CH2:31]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:22]([O:26][C:27](=[O:28])[NH:29][C:30]1([C:33]([NH:2][C:3](=[O:21])[CH2:4][C:5]2[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7][CH:6]=2)=[O:34])[CH2:31][CH2:32]1)([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 16214867HCID 16214867, compound

Product 1

HCID 131731738HCID 131731738, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-hydroxy-2-(4-(4-phenylbutyl)phenyl)acetamide 174 (1 equiv, 156 mg, 0.55 mmol) was dissolved in DMF (3 mL). 1-(tert-butoxycarbonylamino)cyclopropanecarboxylic acid (1.5 equiv, 166 mg, 0.83 mmol) was then added followed by the sequential addition of HOBt (1 equiv, 74 mg, 0.55 mmol) and EDC (1.5 equiv, 158 mg, 0.83 mmol). The reaction was then stirred overnight. The reaction was then partitioned between EtOAc (5 mL) and H2O (5 mL). The organic phase was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by trituration with Et2O to afford tert-butyl-1-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)cyclopropylcarbamate in 166 mg (65%). LRMS: 466.5 (calc) 489.3 (MNa)+.

Workup

  1. customThe reaction was then partitioned between EtOAc (5 mL) and H2O (5 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by trituration with Et2O

Sources & evidence

ORD record
ord-78b09a34a93b4cdcadf5cbc0197517ea
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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