HCID 68453297, compound → HCID 68454248, compound

HRID 2114364Notes

Reaction equation

HRID 2114364 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([C@@:7]([C:17]([O:19][C:20](C)(C)C)=[O:18])([CH3:16])[NH:8]C(OC(C)(C)C)=O)=[CH:3][CH:2]=1>C(Cl)Cl.Cl>[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:6]=[CH:5][C:4]([C@@:7]([C:17]([O:19][CH3:20])=[O:18])([CH3:16])[NH2:8])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 68453297HCID 68453297, compound

Product 1

HCID 68454248HCID 68454248, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

HCl (7.2 ml, 4M in dioxane) was added dropwise to a solution of 1,1-dimethylethyl 2-(4-biphenylyl)-N-{[(1,1-dimethylethyl)oxy]carbonyl}alaninate (1.14 g, 2.87 mmol) in CH2Cl2 (10 ml) at 0° C. under argon. The resulting mix was stirred at room temperature for 16 h. The reaction mixture was concentrated leaving a white solid which was refluxed in methanolic HCl (30 mL) for 16 h. The reaction mixture was concentrated and the residue was taken into Na2CO3 (10%, 100 ml) and the product was extracted by EtOAc (3×20 ml). The combined extracts were washed by water then brine, dried and concentrated left 830 mg as a clear oil. MS(ES) m/e 256.2 [M+H]+.

Workup

  1. additionThe resulting mix
  2. concentrationThe reaction mixture was concentrated
  3. customleaving a white solid which
  4. concentrationThe reaction mixture was concentrated
  5. extractionthe product was extracted by EtOAc (3×20 ml)
  6. washThe combined extracts were washed by water
  7. dry with materialbrine, dried
  8. concentrationconcentrated
  9. waitleft 830 mg as a clear oil

Sources & evidence

ORD record
ord-2ccadad467144da79b32574e63e86312
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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