Carbon Dioxide → HCID 70802833, compound

HRID 475436Notes

Reaction equation

HRID 475436 reaction equation
Br[C:2]1[CH:32]=[CH:31][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C@@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[N:7][O:8][C:4]=2[CH:3]=1.[H-].[Na+].C([Li])CCC.[C:40](=[O:42])=[O:41].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)C.O>[C:26]([O:25][C:24]([NH:23][C@H:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[C:5]2[CH:31]=[CH:32][C:2]([C:40]([OH:42])=[O:41])=[CH:3][C:4]=2[O:8][N:7]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:30])([CH3:28])([CH3:29])[CH3:27]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 311Citric AcidHCID 24758Sodium hydrideHCID 70802488HCID 70802488, compound2×HCID 178418339Butyllithium

Product 1

HCID 70802833HCID 70802833, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of tert-butyl 1-(S)-(2-(6-bromobenzo[d]isoxazol-3-yl)phenyl)-2-(pyridin-2-yl)ethylcarbamate (Compound 16a) (1.72 g) in diethyl ether (30 mL) at 5° C. was added a 60% dispersion in mineral oil of sodium hydride (3.34 g). The suspension was stirred at 5° C. for 10 min and then cooled to −65° C. and a 2.5M solution of n-butyllithium in hexanes (5.57 mL) was added. The suspension was stirred at −70° C. for 30 min and then poured onto solid carbon dioxide pellets and left to stand until the mixture reached room temperature. To this was added water and acidified with citric acid and extracted with ether (3×200 mL), the organic layers were dried over anhydrous magnesium sulfate and evaporated. Flash chromatography eluting with 10% methanol in dichloromethane to give the title product (0.71 g).

Workup

  1. temperaturecooled to −65° C.
  2. stirringThe suspension was stirred at −70° C. for 30 min
  3. waitleft
  4. customreached room temperature
  5. extractionextracted with ether (3×200 mL)
  6. dry with materialthe organic layers were dried over anhydrous magnesium sulfate
  7. customevaporated
  8. washFlash chromatography eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-011b555c105f42d897a3fb2216007c24
Source dataset
uspto-grants-2014_01
Patent number
US08637551B2

Reaction notes

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