Hydrochloric Acid → LY-2886721 hydrochloride

HRID 2060799Notes

Reaction equation

HRID 2060799 reaction equation
[ClH:1].O1CCOCC1.[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([F:41])=[C:22]([C:24]34[CH2:32][O:31][CH2:30][CH:29]3[CH2:28][S:27][C:26]([NH:33]C(=O)OC(C)(C)C)=[N:25]4)[CH:23]=2)=[O:16])=[N:13][CH:14]=1>>[ClH:1].[NH2:33][C:26]1[S:27][CH2:28][C@@H:29]2[CH2:30][O:31][CH2:32][C@:24]2([C:22]2[CH:23]=[C:18]([NH:17][C:15](=[O:16])[C:12]3[CH:11]=[CH:10][C:9]([F:8])=[CH:14][N:13]=3)[CH:19]=[CH:20][C:21]=2[F:41])[N:25]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66861447tert-butyl 7a-(5-(5-fluoropicolinamido)-2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-ylcarbamate

Product 1

HCID 50902942LY-2886721 hydrochloride

Procedure

A solution of 4M hydrogen chloride in dioxane (834.8 μL; 3.3 mmol) is added to tert-butyl 7a-(5-(5-fluoropicolinamido)-2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-ylcarbamate (91 mg; 167.0 μmol) and stirred at ambient temperature. After 2 days, the reaction mixture is concentrated in vacuo. The residue is dissolved in minimal dichloromethane and methanol. Ether and hexane are added. The product is precipitated as the salt which is separated from the mother liquor by centrifugation and placed under vacuum to remove any solvent present to give the title compound (58 mg; 125 mmol). LC-ES/MS m/e 391 (M+1); TR=1.675.

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in minimal dichloromethane
  3. additionEther and hexane are added
  4. customThe product is precipitated as the salt which
  5. customis separated from the mother liquor by centrifugation
  6. customto remove any solvent present

Sources & evidence

ORD record
ord-4b610497dc484389b31c7f6db86e1fe1
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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