1,4-Dioxane → HCID 67435825, compound

HRID 1946536Notes

Reaction equation

HRID 1946536 reaction equation
CC([CH:5]([O:9][CH:10]1[C:19]2[N:18]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=3)[C:17]([CH:29]([CH3:31])[CH3:30])=[N:16][C:15]=2[CH2:14][CH2:13][CH2:12][CH2:11]1)[C:6]([O-:8])=[O:7])(C)C.O1CCOCC1>Cl>[ClH:27].[Cl:28][C:23]1[CH:22]=[C:21]([CH2:20][N:18]2[C:19]3[CH:10]([O:9][CH2:5][C:6]([OH:8])=[O:7])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=3[N:16]=[C:17]2[CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=1[Cl:27]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 86761777HCID 86761777, compound

Product 1

HCID 67435825HCID 67435825, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Intermediate 71 (0.210 g) was stirred in HCl (0.899 mL) and 1,4-Dioxane (0.9 mL) for 1 hour under an atmosphere of Nitrogen. The reaction was allowed to stir overnight. LCMS showed 60% conversion to the product. The reaction mixture was allowed to stir over a second night. LCMS showed further conversion to the product. The sample was concentrated in vacuo and then re-dissolved in 2 mL of a 1:1 mixture of ACN:H2O. An aminopropyl column was washed with 2 CV of ACN:H2O (1:1), then the sample was loaded onto the column. The column was washed with 3 CV of ACN:H2O (1:1). The product was eluted with 3CV of 2N HCl. The appropriate fraction was concentrated in vacuo to give the product. There is an impurity (about 10%) which has the m/z of the methyl ester of the product.

Workup

  1. stirringto stir over a second night
  2. concentrationThe sample was concentrated in vacuo
  3. dissolutionre-dissolved in 2 mL of a 1:1 mixture of ACN
  4. washAn aminopropyl column was washed with 2 CV of ACN:H2O (1:1)
  5. washThe column was washed with 3 CV of ACN:H2O (1:1)
  6. washThe product was eluted with 3CV of 2N HCl
  7. concentrationThe appropriate fraction was concentrated in vacuo
  8. customto give the product

Sources & evidence

ORD record
ord-b193b435f1f7444aac794e608d380fc6
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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