Toluene → HCID 71503471, compound

HRID 625166Notes

Reaction equation

HRID 625166 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:24][CH2:25][C@@H:26]([O:29][C@@H:30]([N:33]2[C:39](=[O:40])[NH:38][C:36](=[O:37])[CH:35]=[CH:34]2)[CH2:31][OH:32])[CH2:27][OH:28])([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.C1(C)C=CC=CC=1.N1C(=O)CC[C@H]1C(O)=O.[C:57](Cl)(=[O:64])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>CCO.C(Cl)Cl>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:9]([O:24][CH2:25][C@@H:26]([O:29][C@@H:30]([N:33]2[C:39](=[O:40])[NH:38][C:36](=[O:37])[CH:35]=[CH:34]2)[CH2:31][O:32][C:57]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[O:64])[CH2:27][OH:28])([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7405L-Pyroglutamic AcidHCID 7412Benzoyl chlorideHCID 71503470HCID 71503470, compound

Product 1

HCID 71503471HCID 71503471, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

Nucleoside 102-U (3.01 g, 5.50 mmol) was coevaporated with an. toluene (15 mL). The resulting residue was dissolved in an. DCM (150 mL) along with an. Pyr. (4.4 mL) and the mixture was cooled to −70° C. Benzoyl chloride (700 μL, 6 mmol) was slowly added to the reaction mixture and stirred for 1 h at −70° C. EtOH (5 mL) was added to the solution and subsequently allowed to reach rt. The reaction mixture was washed with sat. aq. NaHCO3 (3×100 mL) and brine (100 mL). The combined aqueous phase was back extracted with CH2Cl2 (100 mL). The organic phases were combined and evaporated. The resulting residue was purified by column chromatography (3.5% MeOH in DCM) affording the product 103-U as a white foam after evaporation of the solvents.

Workup

  1. dissolutionThe resulting residue was dissolved in an
  2. customto reach rt
  3. washThe reaction mixture was washed with sat. aq. NaHCO3 (3×100 mL) and brine (100 mL)
  4. extractionThe combined aqueous phase was back extracted with CH2Cl2 (100 mL)
  5. customevaporated
  6. customThe resulting residue was purified by column chromatography (3.5% MeOH in DCM)

Sources & evidence

ORD record
ord-97504f658add4de9ac41c1f3ac536245
Source dataset
uspto-grants-2016_04
Patent number
US09303260B2

Reaction notes

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