Triethylamine → HCID 118495853, compound

HRID 876569Notes

Reaction equation

HRID 876569 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][C@H:11]([C@@H:15]([OH:27])[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)=[O:17])[C:10]2=[O:28])[CH:5]=[CH:6][C:7]=1[CH3:8].C(N(CC)CC)C.[C:36]([O:39][CH2:40][C:41](Cl)=[O:42])(=[O:38])[CH3:37].CCOC(C)=O>C(Cl)Cl.O>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16](=[O:17])[C@@H:15]([C@H:11]2[O:12][CH2:13][CH2:14][N:9]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH:3]=3)[NH:1][C:41](=[O:42])[CH2:40][O:39][C:36](=[O:38])[CH3:37])[C:10]2=[O:28])[OH:27])=[CH:20][CH:21]=1)#[N:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 26297Acetoxyacetyl chlorideHCID 67221778HCID 67221778, compound

Product 1

HCID 118495853HCID 118495853, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 9-5 (16.5 mg) in CH2Cl2 (1 mL), were added triethylamine (6.7 microL) and acetoxyacetyl chloride (5.1 microL) at 0° C. The reaction mixture was stirred at room temperature for 30 minutes. Then EtOAc and water were added into the mixture and it was extracted with EtOAc. The organic layer was washed with H2O, 1N HCl, sat. NaHCO3 aq. and brine, respectively and dried with anhydr. Na2SO4. The solvent was removed under reduced pressure to obtain compound 9-6 (20 mg) as a pale yellow amorphous solid.

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with H2O, 1N HCl, sat. NaHCO3 aq. and brine
  3. customrespectively and dried with anhydr
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cf894cdd2f944b248f4cd7f2bfece442
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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