4-tert-Butylbenzoic acid → HCID 59830371, compound

HRID 1619747Notes

Reaction equation

HRID 1619747 reaction equation
[C:1]1([C:7]2[CH2:11][C:10]3([CH2:16][CH2:15][NH:14][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:59]([C:63]1[CH:71]=[CH:70][C:66]([C:67](O)=[O:68])=[CH:65][CH:64]=1)([CH3:62])([CH3:61])[CH3:60]>CCOC(C)=O.C1COCC1>[C:59]([C:63]1[CH:64]=[CH:65][C:66]([C:67]([N: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:68])=[CH:70][CH:71]=1)([CH3:62])([CH3:60])[CH3:61]

Participants

8

Reactant 5

HCID 74034-tert-Butylbenzoic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 39083045HCID 39083045, compound

Product 1

HCID 59830371HCID 59830371, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene (E) was slowly added as a hydrochloride salt (250 mg) to a solution of N-ethyldiisopropylamine (560 μl, 3 mmol), 1-hydroxybenzotriazole hydrate (133 mg, 1 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (318 mg, 1 mmol) and 4-tert-butylbenzoic acid (176 mg, μmol) in abs. THF (8 ml). The reaction mixture was stirred overnight and diluted with EtOAc. The organic phase was washed successively with sat. aq. NaCl solution, sat. aq. NaHCO3 solution, sat. aq. NaCl solution and sat. aq. NH4Cl solution and the solvent removed under vacuum. The desired product (4-tert-butylphenyl)-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)methanone was obtained in a yield of 0.42 g.

Workup

  1. washThe organic phase was washed successively with sat. aq. NaCl solution, sat. aq. NaHCO3 solution, sat. aq. NaCl solution and sat. aq. NH4Cl solution
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-0b7c096b9e4f47ecb48287aaa68f0fe6
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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