p-Toluenesulfonic acid → HCID 67387283, compound

HRID 1027138Notes

Reaction equation

HRID 1027138 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:5][OH:6].[O:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:4]1[N:7]([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])[C:22]2([CH2:23][CH2:24][O:19][CH2:20][CH2:21]2)[O:6][CH2:5]1)=[O:18]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 121599Tetrahydro-4H-pyran-4-oneHCID 323417Methyl N-[(benzyloxy)carbonyl]serinate

Product 1

HCID 67387283HCID 67387283, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Benzyloxycarbonylamino-3-hydroxy-propionic acid methyl ester (2.0 g, 7.9 mmol) was combined with tetrahydro-pyran-4-one (790 mg, 7.9 mmol). This mixture was dissolved in 120 mL of dry toluene. Catalytic amount (50 mg) of p-toluenesulfonic acid was then added to the reaction mixture which was heated under reflux overnight. It was brought to room temperature, diluted using EtOAc, and extracted using NaHCO3. Organic phase was isolated, dried over Na2SO4 and evaporated. The resulting clear oil was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customwas brought to room temperature
  4. additiondiluted
  5. extractionextracted
  6. customOrganic phase was isolated
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customThe resulting clear oil was used in the next step without further purification

Sources & evidence

ORD record
ord-57174259580f42c4805b28b7b90611ba
Source dataset
uspto-grants-2014_05
Patent number
US08729077B2

Reaction notes

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