Water → HCID 22258038, compound

HRID 1611025Notes

Reaction equation

HRID 1611025 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([S:23]([O-:25])=[O:24])=[C:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[S:11][C:5]=2[N:4]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:3]1=[O:30].[Li+].Cl[N:33]1C(=O)C[CH2:35][C:34]1=O.[OH2:40]>ClCCl.Cl>[OH:40][CH2:35][CH2:34][NH:33][S:23]([C:9]1[C:6]2[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:30])[N:4]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:5]=2[S:11][C:10]=1[CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 23705461HCID 23705461, compound

Product 1

HCID 22258038HCID 22258038, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-Chlorosuccinimde (52 mg) was added to a rapidly stirred suspension of lithium 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-sulfinate (200 mg) in dichloromethane (8 ml) and 0.22M hydrochloric acid (9 ml). After 1 hour, further N-chlorosuccinimide (26 mg) was added. After 1 hour, water (30 ml) and dichloromethane (30 ml) were added and the phases were separated. The aqueous phase was extracted with dichloromethane (2×10 ml). The combined organic extracts were treated with ethanolamine (0.071 ml). After 30 minutes, the solution was washed with saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ether to give the title compound (120 mg) as a foam.

Workup

  1. waitAfter 1 hour
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with dichloromethane (2×10 ml)
  4. additionThe combined organic extracts were treated with ethanolamine (0.071 ml)
  5. waitAfter 30 minutes
  6. washthe solution was washed with saturated sodium hydrogen carbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography over silica
  11. washeluting with ether

Sources & evidence

ORD record
ord-40d6e5d499e54a2d9528e3d369a8b6cc
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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