HCID 86630970, compound → HCID 86630969, compound

HRID 874843Notes

Reaction equation

HRID 874843 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([OH:23])[C:9]2[C@@H:15]3[CH:16]=[C:17]([CH3:20])[CH2:18][CH2:19][C@H:14]3[C:13]([CH3:22])([CH3:21])[O:12][C:10]=2[CH:11]=1.[N+](C1C=CC=CC=1S[NH:34][CH2:35][C:36]([O-:38])=[O:37])([O-])=O>ClCCl.C1(S)C=CC=CC=1.C(O)(C(F)(F)F)=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([OH:23])[C:9]2[C@@H:15]3[CH:16]=[C:17]([CH3:20])[CH2:18][CH2:19][C@H:14]3[C:13]([CH3:22])([CH3:21])[O:12][C:10]=2[CH:11]=1.[NH2:34][CH2:35][C:36]([O-:38])=[O:37]

Participants

5

Reactant 1

HCID 86630970HCID 86630970, compound

Product 1

HCID 86630969HCID 86630969, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 7969ThiophenolSolvent

Procedure

THC N-(2-nitrophenylsulfenyl)glycinate (6.1 mg, 0.0116 mmol) was dissolved at ambient temperature in dry dichloromethane containing 10% (v/v) of thiophenol and 1.5% (v/v) of TFA (100 μl). After 5 min the mixture was quenched by addition of 120 μL 3% triethylamine in DCM (at 0° C.). The solution of crude product was chromatographed directly on silica gel with dichloromethane-methanol (gradient 1:0, 20:1, 10:1, 5:1). The combined fractions containing the product were diluted with chloroform, concentrated at 25° C. to ˜3 mL, diluted with chloroform and concentrated again to ˜0.5 mL. The solution of product was diluted with chloroform again (˜5 mL) and concentrated to dryness. Remaining oil was immediately dissolved in chloroform, concentrated to dryness (2.49 mg, 58%), and immediately dissolved in chloroform to afford a stock solution of THC glycinate (ALL00130) stored at −20° C.

Workup

  1. customAfter 5 min the mixture was quenched by addition of 120 μL 3% triethylamine in DCM (at 0° C.)
  2. customThe solution of crude product was chromatographed directly on silica gel with dichloromethane-methanol (gradient 1:0, 20:1, 10:1, 5:1)
  3. additionThe combined fractions containing the product
  4. additionwere diluted with chloroform
  5. concentrationconcentrated at 25° C. to ˜3 mL
  6. additiondiluted with chloroform
  7. concentrationconcentrated again to ˜0.5 mL
  8. additionThe solution of product was diluted with chloroform again (˜5 mL)
  9. concentrationconcentrated to dryness
  10. dissolutionwas immediately dissolved in chloroform
  11. concentrationconcentrated to dryness (2.49 mg, 58%)
  12. dissolutionimmediately dissolved in chloroform

Sources & evidence

ORD record
ord-77044b4f0b444dc683fa12331e4a5e0b
Source dataset
uspto-grants-2015_03
Patent number
US08980942B2

Reaction notes

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