HCID 67138409, compound → HCID 67139914, compound

HRID 1592034Notes

Reaction equation

HRID 1592034 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]([NH:23]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1>C(Cl)Cl.FC(F)(F)C(O)=O>[CH3:1][O:2][C:3](=[O:31])[CH:4]([NH2:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 67138409HCID 67138409, compound

Product 1

HCID 67139914HCID 67139914, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of the title F compound, 3-(3-benzyloxy-4-nitro-phenyl)-2-t-butyloxycarbonylamino-propionic acid methyl ester (733 mg, 1.7 mmol) in a mixture of CH2Cl2-trifluoroacetic acid (1:1, 7 mL) is stirred at RT for 30 min, then evaporated. The residue is partitioned between EtOAc and saturated aqueous NaHCO3. The layers are separated and the aqueous layer is extracted once more with EtOAc. The combined organic extracts are washed with brine, dried over anhydrous MgSO4, filtered and evaporated to give 3-(3-benzyloxy-4-nitro-phenyl)-2-amino-propionic acid methyl ester as a viscous yellow oil.

Workup

  1. customevaporated
  2. customThe residue is partitioned between EtOAc and saturated aqueous NaHCO3
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted once more with EtOAc
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d5033d10e1d74f2c965bf580f2e7552e
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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