Trifluoroacetic acid → HCID 86585123, compound

HRID 636145Notes

Reaction equation

HRID 636145 reaction equation
C(OC([NH:8][C@@H:9]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=2)[CH:14]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.F[C:26](F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@@H:9]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=2)[CH:14]=1)[C:10]([O:12][CH3:26])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69623028HCID 69623028, compound

Product 1

HCID 86585123HCID 86585123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-(tert-Butoxycarbonylamino)-2-(6-methoxy-2-naphthyl)acetic acid was then converted into the methyl ester using General Procedure G below. The methyl ester was then dissolved in CH2Cl2 and this solution cooled to 0° C. Trifluoroacetic acid (50 molar eq.) was added and the reaction was allowed to warm to room temperature and stirring was continued for 2 hrs. The reaction mixture was then concentrated and the residue extracted into CH2Cl2 and washed with sodium bicarbonate solution. The organic layer was dried over Na2SO4, filtered and concentrated to yield methyl (S)-2-amino-2-(6-methoxy-2-naphthyl)acetate.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe reaction mixture was then concentrated
  3. extractionthe residue extracted into CH2Cl2
  4. washwashed with sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1151ce47e5ec4e02974657a3eaf81f2d
Source dataset
uspto-grants-2001_02
Patent number
US06191166B1

Reaction notes

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