Trifluoroacetic acid → HCID 86585123, compound

HRID 983247Notes

Reaction equation

HRID 983247 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-cfcceb03d2774e358b298c641dd6854e
Source dataset
uspto-grants-2005_03
Patent number
US06861558B2

Reaction notes

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