Hydrochloric Acid → HCID 21931913, compound

HRID 1453926Notes

Reaction equation

HRID 1453926 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH2:16]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([OH:22])(=[O:21])[CH2:19][SH:20].B(F)(F)F.[CH3:27][CH2:28]OCC.Cl>ClCCCl.O>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH2:16][S:20][CH2:19][C:18]([O:22][CH2:27][CH3:28])=[O:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 8000Boron trifluoride etherateHCID 11770077HCID 11770077, compound

Product 1

HCID 21931913HCID 21931913, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

A 250 mL round-bottom flask containing a magnetic stirring bar equipped with a reflux condenser was charged with 1.6 g (0.00717 mol) of compound 62, 0.8 mL (0.00717 mol) of thioglycolic acid and 50 mL of 1,2-dichloroethane. At 0° C., 1.4 mL (0.0107 mol) of BF3.Et2O dissolved in 10 mL of 1,2-dichloroethane was added slowly. The resulting mixture was stirred for 15 minutes and then 100 mL of water and 10 mL of HCl (1N) were added. The product was extracted with 2×50 mL of ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness. The crude product was used for the next step (preparation of Example 148).

Workup

  1. additionA 250 mL round-bottom flask containing a magnetic stirring bar
  2. customequipped with a reflux condenser
  3. additionwas added slowly
  4. extractionThe product was extracted with 2×50 mL of ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product was used for the next step (preparation of Example 148)

Sources & evidence

ORD record
ord-7742bed10df5433ba131daa37775c7d0
Source dataset
uspto-grants-2009_01
Patent number
US07476690B2

Reaction notes

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