Thionyl Chloride → HCID 59556148, compound

HRID 1809916Notes

Reaction equation

HRID 1809916 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-06d15cea4cba47de863805438a322346
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

Loading…