Benzoic Acid → HCID 67156794, compound

HRID 221586Notes

Reaction equation

HRID 221586 reaction equation
[C:1]([NH:20][C@H:21]([C:25]([O:27][CH3:28])=[O:26])[C@@H:22]([CH3:24])[OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](O)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>CCOCC.C(OCC)(=O)C.C1COCC1>[C:29]([O:23][C@@H:22]([CH3:24])[C@@H:21]([C:25]([O:27][CH3:28])=[O:26])[NH:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

10

Reactant 6

HCID 243Benzoic AcidHCID 1140TolueneHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 5462977Diethyl azodicarboxylateHCID 11025190Methyl trityl-L-threoninate

Product 1

HCID 67156794HCID 67156794, compoundYield 25.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 500-mL, round-bottomed flask was charged with methyl N-trityl-L-threoninate (3.75 g, 10.0 mmol), benzoic acid (2.44 g, 20.0 mmol) and triphenylphosphine (5.24 g, 20.0 mmol). Anhydrous THF (50 mL) was added and the solution was cooled to 0° C. under N2 with stirring. A 40% solution of diethylazodicarboxylate in toluene (9.06 mL, 20.0 mmol) was added dropwise and the reaction mixture was allowed to warm to ambient temperature overnight. The reaction mixture was treated with 50 mL of ethyl acetate and 50 mL of saturated aqueous NaHCO3 solution. The layers were separated and the organic portion was washed successively with H2O and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give a yellow syrup. The yellow syrup was dissolved in 25 mL of Et2O and then treated with hexanes until a white precipitate formed. The solid was removed by filtration and the filtrate was concentrated to give a yellow oil. Chromatography (SiO2, 33-100% CH2Cl2/hexanes) gave 1.24 g of methyl O-benzoyl-N-trityl-L-allothreoninate as a colorless solid.

Workup

  1. temperatureto warm to ambient temperature overnight
  2. customThe layers were separated
  3. washthe organic portion was washed successively with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow syrup
  8. customformed
  9. customThe solid was removed by filtration
  10. concentrationthe filtrate was concentrated
  11. customto give a yellow oil

Sources & evidence

ORD record
ord-ef19949dc8f442d6af96be07003c46e2
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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