(4-Oxazol-5-yl-naphthalen-1-yl)-carbamic acid tert-butyl ester → 4-Oxazol-5-yl-naphthalen-1-ylamine

HRID 2110464Notes

Reaction equation

HRID 2110464 reaction equation
C(OC(=O)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[O:22][CH:21]=[N:20][CH:19]=2)=[CH:10][CH:9]=1)(C)(C)C>FC(F)(F)C(O)=O>[O:22]1[C:18]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([NH2:7])=[CH:9][CH:10]=2)=[CH:19][N:20]=[CH:21]1

Participants

3

Reactant 1

HCID 58745848(4-Oxazol-5-yl-naphthalen-1-yl)-carbamic acid tert-butyl ester

Product 1

HCID 218750874-Oxazol-5-yl-naphthalen-1-ylamineYield 99.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 503C (1.34 g, 4.3 mmol) was dissolved in trifluoroacetic acid (10 mL) and the resulting mixture was allowed to stand for 1 h at room temperature. After removing the volatiles in vacuo, the residue was co-evaporated from ethyl acetate/heptane (2×50 mL) to remove traces of trifluoroacetic acid. After partitioning the residue between ethyl acetate (100 mL) and 1N NaOH (75 mL), the organic layer was washed with brine (50 mL), dried over magnesium sulfate and concentrated in vacuo to afford 900 mg (99%) of compound 503D as a yellow crystalline solid. HPLC conditions: 95% at 0.92 min (retention time) (Phenomenex 5 micron ODScolumn, 4.6×30 mm, 10%-90% aqueous methanol over 2 min gradient with 0.1% TFA, monitoring at 254 nm.). MS (ES): m/z 211.22 [M+H]+.

Workup

  1. customAfter removing the volatiles in vacuo
  2. customto remove traces of trifluoroacetic acid
  3. customAfter partitioning the residue between ethyl acetate (100 mL) and 1N NaOH (75 mL)
  4. washthe organic layer was washed with brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b50d71c1bf664688bf6ca2bfc97fdb84
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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