Water → HCID 18510695, compound

HRID 2219091Notes

Reaction equation

HRID 2219091 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C@H:18]2[O:22][N:21]=[C:20]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH2:19]2)=[O:17])=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC1C=CC(C2C=CC=CC=2C[C:43]([O:45][CH3:46])=[O:44])=CC=1.CC(N(C(C)C)CC)C.O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:20]2[CH2:19][CH:18]([C:16]([NH:15][C:12]3[CH:13]=[CH:14][C:9]([CH:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:43]([O:45][CH3:46])=[O:44])=[CH:10][CH:11]=3)=[O:17])[O:22][N:21]=2)[CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 53672405HCID 53672405, compoundHCID 86590905HCID 86590905, compound

Product 1

HCID 18510695HCID 18510695, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

) Intermediate (3) (0.007 mol) was added to a solution of methyl [(4-aminophenyl) phenyl]acetate (0.007 mol), N,N-bis(1-methylethyl)ethanamine (0.014 mol) and N,N-dimethyl-4-pyridinamine (catalytic quantity) in CH2Cl2 (100 ml), stirred at 0° C. The reaction mixture was stirred overnight at RT. Water was added. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated under reduced pressure. The residue was crystallized from EtOAc. The precipitate was filtered off, washed with EtOAc, and dried, yielding 1.0 g (35%) of (±)-methyl 4-[[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]carbonyl]amino]-α-phenylbenzeneacetate (compound 56).

Workup

  1. stirringThe reaction mixture was stirred overnight at RT
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was crystallized from EtOAc
  10. filtrationThe precipitate was filtered off
  11. washwashed with EtOAc
  12. customdried

Sources & evidence

ORD record
ord-d8428fb05e354f08901af10f52d2d094
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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