HCID 69365026, compound → HCID 58654504, compound

HRID 1170483Notes

Reaction equation

HRID 1170483 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10](=[O:23])[NH:11][CH2:12][CH2:13][C:14]1[CH:22]=[CH:21][C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1)[CH3:9])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:7][C@@H:8]([CH3:9])[C:10]([NH:11][CH2:12][CH2:13][C:14]1[CH:22]=[CH:21][C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1)=[O:23]

Participants

3

Reactant 1

HCID 69365026HCID 69365026, compound

Product 1

HCID 58654504HCID 58654504, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

[1-(2-Benzo[1,3]dioxol-5-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (350 mg, 1.04 mmol) was dissolved in TFA:DCM (1:1, 4 mL) and allowed to stir at room temperature for 2 h. After this time, the solution was concentrated down under N2 gas and dissolved in DCM. The solution was washed several times with 1M NaOH (aq). The organic layer was dried with Na2SO4 and concentrated down under N2. The crude material was purified by flash chromatography (DCM to 9:1 DCM/MeOH) to afford 189 mg (77% yield) of (S)-2-amino-N-(2-benzo[1,3]dioxol-5-yl-ethyl)-propionamide. [M+H]+ 237.10.

Workup

  1. concentrationAfter this time, the solution was concentrated down under N2 gas
  2. dissolutiondissolved in DCM
  3. washThe solution was washed several times with 1M NaOH (aq)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated down under N2
  6. customThe crude material was purified by flash chromatography (DCM to 9:1 DCM/MeOH)

Sources & evidence

ORD record
ord-28b45abb214144d2bba0c6dbe09279de
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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