Water → 2-Methylpentane

HRID 2201255Notes

Reaction equation

HRID 2201255 reaction equation
[Cl:1][C:2]1[O:6][C:5]([CH:7]2[C:12]3=[C:13]4[N:29]([CH3:30])[C:28](=[O:31])[N:27]([CH3:32])[C:26](=[O:33])[C:14]4=[C:15]([C:16]4[S:17][CH:18]=[C:19]([C:21]([O:23]CC)=[O:22])[N:20]=4)[N:11]3[CH2:10][CH2:9][S:8]2)=[CH:4][CH:3]=1.O.[OH-].[Li+].O>C1COCC1>[CH3:7][CH2:12][CH2:13][CH:14]([CH3:26])[CH3:15].[Cl:1][C:2]1[O:6][C:5]([CH:7]2[C:12]3=[C:13]4[N:29]([CH3:30])[C:28](=[O:31])[N:27]([CH3:32])[C:26](=[O:33])[C:14]4=[C:15]([C:16]4[S:17][CH:18]=[C:19]([C:21]([OH:23])=[O:22])[N:20]=4)[N:11]3[CH2:10][CH2:9][S:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrate2×HCID 86723494HCID 86723494, compound

Product 2

HCID 78922-MethylpentaneHCID 77107425HCID 77107425, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(10-(5-chlorofuran-2-yl)-1,3-dimethyl-2,4-dioxo-2,3,4,7,8,10-hexahydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]thiazin-5-yl)thiazole-4-carboxylate (Example 15 Step 1)(72 mg, 0.142 mmol) and lithium hydroxide monohydrate (5.96 mg, 0.142 mmol) were suspended in THF (5 mL) and the mixture stirred at room temperature for 24 hours. Two portions of lithium hydroxide monohydrate (5.96 mg, 0.142 mmol) were added during this period. Water (2 mL) was then added and the mixture stirred for a further 30 mins. The resulting mixture was evaporated under vacuum. The residue was partitioned between water (20 ml) and DCM (20 mL) and brought to pH 1 with HCl(aq). The phases were separated and the aqueous phase was extracted with DCM (2×20 ml). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum. The residue was re-suspended in DCM (5 ml) and loaded to a Isolute PE-AX ion exchange cartridge (1 g). The cartridge was eluted with DCM (50 ml), 1:1 MeOH:DCM (20 ml) and 4 M HCl/dioxane. The acidic eluent was evaporated under vacuum and the residue triturated with TBME:iso-hexane to afford the title compound.

Workup

  1. stirringthe mixture stirred for a further 30 mins
  2. customThe resulting mixture was evaporated under vacuum
  3. customThe residue was partitioned between water (20 ml) and DCM (20 mL)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with DCM (2×20 ml)
  6. customevaporated under vacuum
  7. washThe cartridge was eluted with DCM (50 ml), 1:1 MeOH
  8. customThe acidic eluent was evaporated under vacuum
  9. customthe residue triturated with TBME

Sources & evidence

ORD record
ord-5998a5c0f9c54cb4b94e7917150d12cb
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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