Triethylamine → HCID 70871888, compound

HRID 470671Notes

Reaction equation

HRID 470671 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@@H:9]2[C@:24]3([C:32]4[C:27](=[CH:28][C:29]([Cl:33])=[CH:30][CH:31]=4)[NH:26][C:25]3=[O:34])[C:16]3([CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH2:18][CH2:17]3)[N:15]3[C@H:10]2[C:11](=[O:47])[O:12][C@@H:13]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:14]3[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:48](N(CC)CC)C.[C:55](=[O:58])(O)[O-:56].[Na+]>CS(C)=O.CO>[Cl:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([C@@H:9]2[C:24]3([C:32]4[C:27](=[CH:28][C:29]([Cl:33])=[CH:30][CH:31]=4)[NH:26][C:25]3=[O:34])[C:16]3([CH2:21][CH2:20][C:19]([CH3:22])([CH3:23])[CH2:18][CH2:17]3)[N:15]3[C@H:10]2[C:11](=[O:47])[O:12][C@@H:13]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C@H:14]3[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:5]=1)[C:55]([O:56][CH3:48])=[O:58]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 70871721HCID 70871721, compound

Product 1

HCID 70871888HCID 70871888, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

The compound (3.14 g, 4.30 mmol) obtained in Step 1 above was dissolved in dimethyl sulfoxide (40 ml) and methanol (40 ml), triethylamine (0.71 ml, 5.16 mmol) and a 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (351 mg, 0.43 mmol) were added and the resulting mixture was stirred under heating at 90° C. for 2 days under carbon monoxide atmosphere. Saturated sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=1:1 (v/v)] to give 0.40 g (13%) of the title compound as a yellow solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=1:1 (v/v)]

Sources & evidence

ORD record
ord-ae6cb0f7fad14c36acc347db80870e5c
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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