4-Tert-Butylaniline → 3-Phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide

HRID 1013341Notes

Reaction equation

HRID 1013341 reaction equation
[C:1]1([C:7]2[CH2:11][C:10]3([CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.O.ON1C2C=CC=CC=2N=N1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:62]([C:66]1[CH:72]=[CH:71][C:69]([NH2:70])=[CH:68][CH:67]=1)([CH3:65])([CH3:64])[CH3:63]>C1COCC1>[C:62]([C:66]1[CH:67]=[CH:68][C:69]([NH:70][C:17]([CH:14]2[CH2:15][CH2:16][C:10]3([O:9][N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:11]3)[CH2:12][CH2:13]2)=[O:19])=[CH:71][CH:72]=1)([CH3:65])([CH3:63])[CH3:64]

Participants

7

Reactant 5

HCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 579514503-Phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid

Product 1

HCID 579514553-Phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid (400 mg, 1.5 mmol) was slowly added to a solution of N-ethyldiisopropylamine (662 mg, 4.6 mmol), 1-hydroxybenzotriazole hydrate (206 mg, 1.5 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (496 mg, 1.5 mmol) and 4-tert-butylaniline (230 mg, 1.5 mmol) in abs. THF (11 ml). The reaction mixture was stirred overnight and the solvent removed under vacuum. The residue was taken up in EtOAc (75 ml). The organic phase was washed successively with sat. aq. NaCl solution, sat. aq. NaHCO3 solution, sat. aq. ammonium sulphate solution and sat. aq. NaCl solution, dried over magnesium sulphate and the solvent removed under vacuum. The desired product 3-phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide was obtained as a diastereomer mixture in a yield of 220 mg (37% of the theoretical amount).

Workup

  1. customthe solvent removed under vacuum
  2. washThe organic phase was washed successively with sat. aq. NaCl solution, sat. aq. NaHCO3 solution, sat. aq. ammonium sulphate solution and sat. aq. NaCl solution
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-46c67fa089eb4a6e99cc3074f495f765
Source dataset
uspto-grants-2011_07
Patent number
US07981883B2

Reaction notes

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