Ethanamine, 2-fluoro-, hydrochloride → 5-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-N-(2-fluoroethyl)isoxazole-3-carboxamide

HRID 880355Notes

Reaction equation

HRID 880355 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33]1[O:37][N:36]=[C:35]([C:38](O)=[O:39])[CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[F:64][CH2:65][CH2:66][NH2:67].CCN(C(C)C)C(C)C>C1COCC1.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33]1[O:37][N:36]=[C:35]([C:38]([NH:67][CH2:66][CH2:65][F:64])=[O:39])[CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667591895-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylic acid

Product 1

HCID 866623755-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-N-(2-fluoroethyl)isoxazole-3-carboxamideYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylic acid (0.45 g, 0.84 mmol) in THF (30 mL) was added TBTU (0.300 g, 1.1 mmol). After stirring for 15 minutes at room temperature, 2-fluoroethylamine hydrochloride (0.1 g, 1 mmol) and DIPEA (0.58 mL) were subsequently added. After stirring overnight, the suspension was diluted with DCM and washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was carefully chromatographed on silica gel eluting with hexane/ethyl acetate 3/1, to provide the title compound (0.46 g, 94% yield).

Workup

  1. stirringAfter stirring overnight
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was carefully chromatographed on silica gel eluting with hexane/ethyl acetate 3/1

Sources & evidence

ORD record
ord-69cf9b3146ae4fb8a0ee8eeeea5c5e93
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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