Dichloromethane → HCID 58654450, compound

HRID 1170528Notes

Reaction equation

HRID 1170528 reaction equation
C(OC(=O)[NH:7][CH:8]([C:12](=[O:25])[NH:13][CH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=1)[CH:9]([CH3:11])[CH3:10])(C)(C)C.C(Cl)Cl>C(O)(C(F)(F)F)=O>[NH2:7][C@H:8]([CH:9]([CH3:11])[CH3:10])[C:12]([NH:13][CH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=1)=[O:25]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 68696493HCID 68696493, compound

Product 1

HCID 58654450HCID 58654450, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

[1-(2-Benzo[1,3]dioxol-5-yl-ethylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester (447.1 mg, 1.23 mmol) was dissolved in 1:1 TFA:DCM (6 mL) and stirred at room temperature for 3 hours. After this time, the solvent was removed by vacuum. The crude material was dissolved in DCM (75 mL) and washed with 1M NaOH (aq) (75 mL) to afford the crude product as the freebase. The product was purified by Flash Chromatography (0-10% methanol/DCM gradient) to afford 270.7 mg (83.5%) of the pure product, 2-amino-N-(2-benzo[1,3]dioxol-5-yl-ethyl)-3-methyl-butyramide. [M+H]+ 265.1

Workup

  1. customAfter this time, the solvent was removed by vacuum
  2. dissolutionThe crude material was dissolved in DCM (75 mL)
  3. washwashed with 1M NaOH (aq) (75 mL)
  4. customto afford the crude product as the freebase
  5. customThe product was purified by Flash Chromatography (0-10% methanol/DCM gradient)

Sources & evidence

ORD record
ord-cf0791dbf9be4e22b4eaf1d803bb4f2f
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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