Ethyl Acetate → HCID 23679692, compound

HRID 1699537Notes

Reaction equation

HRID 1699537 reaction equation
C(OC([O:7][C@@H:8]([C@H:10]1[C:42](=[O:43])[N:12]2[C:13]([C:36]([O:38]CC=C)=[O:37])=[C:14]([CH2:17][N:18]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[S:19]3(=[O:35])=[O:34])[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[Na+:73].C(OCC)(=O)C>C(C(CCCC)C(O)=O)C.C(OCC)C.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.ClCCl.C(OCC)(=O)C>[O:35]=[S:19]1(=[O:34])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[N:27][N:18]1[CH2:17][C:14]1[C@H:15]([CH3:16])[C@@H:11]2[C@@H:10]([C@H:8]([OH:7])[CH3:9])[C:42](=[O:43])[N:12]2[C:13]=1[C:36]([O-:38])=[O:37].[Na+:73]

Participants

9

Reactant 4

HCID 8857Ethyl Acetate2×HCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 131723116HCID 131723116, compound

Product 1

HCID 23679692HCID 23679692, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 86972-Ethylhexanoic AcidSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The product from step 1 (26 mg, 0.043 mmol), triphenylphosphine (4.0 mg, 0.015 mmol), 0.5M sodium 2-ethyl-hexanoate in ethyl acetate (0.095 mL, 0.048 mmol), and 0.5M 2-ethyl-hexanoic acid in ethyl acetate (0.095 mL, 0.048 mmol) were dissolved in 1:1 dichloromethane-ethyl acetate (1.5 mL). Tetrakis(triphenylphosphine)palladium(0) (6 mg, 0.005 mmol) was added and the resulting mixture was stirred at room temperature for 15 minutes. The mixture was diluted with diethyl ether and extracted with water (2 mL). The aqueous extracts were purified by preparative layer chromatography on a 1 mm×20 cm×20 cm RPSF plate, using 3:1 water-acetonitrile as the developing solvent. The product band was located by UV, removed and eluted with 4:1 acetonitrile-water. The eluent was concentrated under vacuum to remove the acetonitrile and lyophilized to afford the title compound (9.7 mg) as an amorphous solid.

Workup

  1. extractionextracted with water (2 mL)
  2. customThe aqueous extracts were purified by preparative layer chromatography on a 1 mm×20 cm×20 cm RPSF plate
  3. customremoved
  4. washeluted with 4:1 acetonitrile-water
  5. concentrationThe eluent was concentrated under vacuum
  6. customto remove the acetonitrile

Sources & evidence

ORD record
ord-7af2d606e55c4fd7a85b13f7b6af3e2d
Source dataset
uspto-grants-2002_02
Patent number
US06346525B1

Reaction notes

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