Diisopropylethylamine → HCID 59170052, compound

HRID 1446301Notes

Reaction equation

HRID 1446301 reaction equation
[C:1]1([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([OH:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([CH:21]2[CH2:25][CH2:24][NH:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:1]1([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([N:23]2[CH2:24][CH2:25][CH:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:22]2)=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 31467433-Phenylpyrrolidine

Product 1

HCID 59170052HCID 59170052, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Phenyl-1,3-oxazole-4-carboxylic acid (40 mg, 0.211 mmol), 3-Phenyl-pyrrolidine (31.6 mg, 0.215 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (86.2 mg, 0.268 mmol) and diisopropylethylamine (25.4 mg, 0.197 mmol) were mixed in dimethylformamide (1.0 mL) and stirred at room temperature. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C20H18N2O2: 318.1368, found 318.1377.

Workup

  1. customSolvent was evaporated in vacuo
  2. filtrationfiltered
  3. custompurified by preparative chromatography
  4. customThe combined fractions were partitioned between NaHCO3 (sat) and ethylacetate
  5. washThe organic layer was washed with water
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfaeba21bfc44542bda392c3c288c234
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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