1-Hydroxybenzotriazole → HCID 86618873, compound

HRID 638963Notes

Reaction equation

HRID 638963 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([CH2:22][CH2:23][CH3:24])[C:19]=1[O:20][CH3:21])[C:6]([N:8]1[CH2:11][C@@H:10]([CH2:12][CH3:13])[C@@H:9]1[C:14]([OH:16])=O)=[O:7].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:69]([O:76][NH2:77])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1>CN(C=O)C.CCOC(C)=O>[CH2:69]([O:76][NH:77][C:14]([C@H:9]1[C@H:10]([CH2:12][CH3:13])[CH2:11][N:8]1[C:6](=[O:7])[C:5]1[CH:17]=[C:18]([CH2:22][CH2:23][CH3:24])[C:19]([O:20][CH3:21])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:16])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68687078HCID 68687078, compound

Product 1

HCID 86618873HCID 86618873, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (+)-trans-1-(3,4-dimethoxy-5-propylbenzoyl)-3-ethylazetidine-2-carboxylic acid (110 mg, 0.33 mmol, 1 eq.) in dry DMF (2.5 mL) were added HATU (150 mg, 0.39 mmol, 1.2 eq.), DIEA (0.23 mL, 1.31 mmol, 4.0 eq.), HOBt (50 mg, 0.39 mmol, 1 eq.) and the mixture was cooled to 0° C. then the O-benzylhydroxylamine hydrochloride (63 mg, 0.39 mmol, 1.2 eq.) was added. The resulting mixture was stirred at 0° C. for 1 h, and then at room temperature overnight. The reaction was diluted with EtOAc, washed with 1M aqueous HCl solution, saturated NaHCO3 solution, and brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give (+)-trans-1-(3,4-dimethoxy-5-propylbenzoyl)-3-ethylazetidine-2-carboxylic acid benzyloxyamide in 68% yield, which was used without further purification. ESMS: m/z 441.3 [M+H].

Workup

  1. customat room temperature
  2. customovernight
  3. washwashed with 1M aqueous HCl solution, saturated NaHCO3 solution, and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81a1c828f9bd4d599e8aa69cb9da2b8e
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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