Thioanisole → HCID 86663394, compound

HRID 2190993Notes

Reaction equation

HRID 2190993 reaction equation
C(OC([NH:8][CH2:9][C:10]1([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH2:16][CH:15]2[CH:11]1[CH:12]=[C:13]([CH2:17][CH3:18])[CH2:14]2)=O)(C)(C)C.C1(SC)C=CC=CC=1.O.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42]([OH:45])(=[O:44])=[O:43])=[CH:38][CH:37]=1>C1C=CC=CC=1>[C:36]1([CH3:46])[CH:37]=[CH:38][C:39]([S:42]([OH:45])(=[O:43])=[O:44])=[CH:40][CH:41]=1.[NH2:8][CH2:9][C:10]1([CH2:19][C:20]([OH:22])=[O:21])[CH2:16][CH:15]2[CH:11]1[CH:12]=[C:13]([CH2:17][CH3:18])[CH2:14]2

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 86761717HCID 86761717, compound

Product 1

HCID 86663394HCID 86663394, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tert-butyl [6-(tert-butoxycarbonylamino)methyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate (1152.23 g, 391.6 mmol) was dissolved in benzene (1.2 L). To the solution, thioanisole (145.57 g, 1173 mmol) and p-toluenesulfonic acid monohydrate (89.39 g) were then added, and the mixture was stirred for 2 hours under reflux. The mixture was left standing overnight at room temperature, and the resulting powder was collected by filtration. The obtained powder was washed with ethyl acetate and then dried to obtain the compound of interest as a white powder (88.29 g, 59%).

Workup

  1. temperatureunder reflux
  2. waitThe mixture was left
  3. waitstanding overnight at room temperature
  4. filtrationthe resulting powder was collected by filtration
  5. washThe obtained powder was washed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-5ae2e4f40fb548aeadac00a2b2942b20
Source dataset
uspto-grants-2012_12
Patent number
US08324425B2

Reaction notes

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