Ethyl Acetate → HCID 86656481, compound

HRID 594181Notes

Reaction equation

HRID 594181 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH2:7][C@@H:8]2[N:14]([CH:15]=1)[C:13](=[O:16])[C:12]1[CH:17]=[C:18]([O:60][CH3:61])[C:19]([O:21][CH2:22][CH2:23][CH2:24][O:25][C:26]3[C:57]([O:58][CH3:59])=[CH:56][C:29]4[C:30](=[O:55])[N:31]5[CH:46]=[C:45]([O:47][S:48]([C:51]([F:54])([F:53])[F:52])(=[O:50])=[O:49])[CH2:44][C@H:32]5[C:33](=[O:43])[N:34]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:28]=4[CH:27]=3)=[CH:20][C:11]=1[N:10]([CH2:62][O:63][CH2:64][CH2:65][Si:66]([CH3:69])([CH3:68])[CH3:67])[C:9]2=[O:70].C([O-])([O-])=O.[Na+].[Na+].[CH3:77][CH2:78]OC(C)=O>C1(C)C=CC=CC=1.CCO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH2:7][C@@H:8]2[N:14]([CH:15]=1)[C:13](=[O:16])[C:12]1[CH:17]=[C:18]([O:60][CH3:61])[C:19]([O:21][CH2:22][CH2:23][CH:24]([O:25][C:26]3[C:57]([O:58][CH3:59])=[CH:56][C:29]4[C:30](=[O:55])[N:31]5[CH:46]=[C:45]([O:47][S:48]([C:51]([F:54])([F:53])[F:52])(=[O:49])=[O:50])[CH2:44][C@H:32]5[C:33](=[O:43])[N:34]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:40])[CH3:41])[C:28]=4[CH:27]=3)[CH2:77][CH3:78])=[CH:20][C:11]=1[N:10]([CH2:62][O:63][CH2:64][CH2:65][Si:66]([CH3:67])([CH3:68])[CH3:69])[C:9]2=[O:70]

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 58388860HCID 58388860, compound

Product 1

HCID 86656481HCID 86656481, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Solid Pd(PPh3)4 (7.66 mg, 6.63 μmol) was added to a stirred, cloudy solution of 14 (174 mg, 0.17 mmol), Na2CO3 (28 mg, 0.22 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)aniline (47 mg, 0.22 mmol) in toluene (2-5 mL), EtOH (1.25 mL) and H2O (125 mL) at room temperature. The reaction mixture was allowed to stir under a N2 atmosphere for 24 hours at which point the reaction was deemed complete by LC/MS major peak (@ 3.97 min, FW=1016, M+Na) and TLC (EtOAc). The solvent was removed by evaporation in vacuo and the resulting residue partitioned between EtOAc (60 mL) and H2O (30 mL). The layers were separated and the organic phase was washed with H2O) (20 mL), brine (30 mL) dried (MgSO4) filtered and evaporated in vacuo to provide the crude product 123 mg, 75% yield.

Workup

  1. customThe solvent was removed by evaporation in vacuo
  2. customthe resulting residue partitioned between EtOAc (60 mL) and H2O (30 mL)
  3. customThe layers were separated
  4. washthe organic phase was washed with H2O) (20 mL), brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-a735c914c59341bcba9d3aac91f38111
Source dataset
uspto-grants-2016_01
Patent number
US09242013B2

Reaction notes

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