Hydrochloric Acid → HCID 67386784, compound

HRID 907952Notes

Reaction equation

HRID 907952 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:11].[O:12]=[C:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14](O)=[O:15].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>ClCCl.O>[O:12]=[C:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:11])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11915Phenylglyoxylic AcidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 67386784HCID 67386784, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminoisobenzofuran-1(3H)-one (4.0 g, 26.8 mmol), 2-oxo-2-phenylacetic acid (4.1 g, 26.8 mmol), and HBTU (15.2 g, 40.2 mmol) in dichloromethane (240 mL) was added TEA (8 mL). The reaction mixture was stirred at room temperature overnight. The resulting mixture was added water and adjusted to pH=6-7 with 1% aq. HCl, and then was filtered. The filtrate was extracted with ethyl acetate. The ethyl acetate layer was evaporated and the crude product was purified by gradient chromatography (silica gel, petroleum ether/ethyl acetate 6:1 to 3:1) to give the title compound (5.0 g, yield 66%). LC-MS (ESI) m/z: 282(M+1)+.

Workup

  1. filtrationwas filtered
  2. extractionThe filtrate was extracted with ethyl acetate
  3. customThe ethyl acetate layer was evaporated
  4. customthe crude product was purified by gradient chromatography (silica gel, petroleum ether/ethyl acetate 6:1 to 3:1)

Sources & evidence

ORD record
ord-055807919d57488ab3138bc6bf39a35a
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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