Thionyl Chloride → HCID 59556148, compound

HRID 1025756Notes

Reaction equation

HRID 1025756 reaction equation
[N:1]1([C:6]([C:8]2[S:12][C:11]([C:13]3(O)[CH2:22][CH2:21][C:16]4([O:20][CH2:19][CH2:18][O:17]4)[CH2:15][CH2:14]3)=[N:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:26])=O>N1C=CC=CC=1>[Cl:26][C:13]1([C:11]2[S:12][C:8]([C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])=[CH:9][N:10]=2)[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][O:17]2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66787618HCID 66787618, compound

Product 1

HCID 59556148HCID 59556148, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 8-[5-(pyrrolidin-1-ylcarbonyl)-1,3-thiazol-2-yl]-1,4-dioxaspiro[4.5]decan-8-ol (0.2 g, 3.32 mmol) in pyridine (3 mL) at 0° C. was added thionyl chloride (0.5 mL, 6.86 mmol) under N2. The mixture was warmed to room temperature and stirred overnight. After the reaction solution was concentrated, water and EtOAc were added. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with saturated NaCl, dried (MgSO4), concentrated and flash chromatographed (50% EtOAc/hexane to EtOAc) to give 0.10 g of the title compound in 53% yield. MS (EI) calcd: (M+1)+=356.1; found: 357.0.

Workup

  1. concentrationAfter the reaction solution was concentrated
  2. additionwater and EtOAc were added
  3. extractionThe aqueous layer was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with saturated NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customflash chromatographed (50% EtOAc/hexane to EtOAc)

Sources & evidence

ORD record
ord-3285ac3a5f384ae092b380550a1713f8
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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