Acetic Anhydride → N-[5-(4-tert-butylphenyl)-1,3-oxazol-2-yl]-N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)acetamide

HRID 600805Notes

Reaction equation

HRID 600805 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([NH:16][C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:26]=3[CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]4)=[N:13][CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:28](OC(=O)C)(=[O:30])[CH3:29].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([N:16]([C:17]3[C:26]4[CH2:25][CH:24]([OH:27])[CH2:23][CH2:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[C:28](=[O:30])[CH3:29])=[N:13][CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 119642568-[5-(4-tert-Butylphenyl)oxazol-2-ylamino]-1,2,3,4-tetrahydronaphthalen-2-ol

Product 1

HCID 11964320N-[5-(4-tert-butylphenyl)-1,3-oxazol-2-yl]-N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)acetamideYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 3C (76 mg, 0.21 mmol) in 2 mL tetrahydrofuran was stirred with acetic anhydride (0.026 mL, 0.275 mmol) and triethylamine (0.088 mL, 0.63 mmol) at rt for 3 h. The reaction mixture was then diluted with ethyl acetate and washed with water and brine. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 35% ethyl acetate-hexane and then 60% ethyl acetate-hexane to afford the title compound as a tan foam (38 mg, 45%). 1H NMR (DMSO-d6) δ 8.03 (s, 1H), 7.48 (m, 4H), 7.10 (m, 2H), 6.82 (m, 1H), 4.72 (d, J=3.8 Hz, 1H), 3.92 (m, 1H), 2.84-3.02 (m, 3H), 2.73 (s, 3H), 2.44 (m, 1H), 1.86 (m, 1H), 1.61 (m, 1H), 1.27 (s, 9H); MS (ESI+) m/z 405 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 35% ethyl acetate-hexane

Sources & evidence

ORD record
ord-cf2da99ed62b45ae872e4c7b795d45a2
Source dataset
uspto-grants-2011_03
Patent number
US07902236B2

Reaction notes

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