Hydrochloric Acid → HCID 10005028, compound

HRID 1374796Notes

Reaction equation

HRID 1374796 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([S:11]([CH3:14])(=[O:13])=[O:12])[C:7]([CH3:15])=[CH:6][CH:5]=2.II.[S:18]1[CH:22]=[CH:21][N:20]=[C:19]1[SH:23].[H-].[Na+].Br[CH2:27][C:28]([O:30]C)=[O:29].[OH-].[Li+].Cl>CN(C=O)C.O>[CH3:1][C:2]1[N:3]([CH2:27][C:28]([OH:30])=[O:29])[C:4]2[C:9]([C:10]=1[S:23][C:19]1[S:18][CH:22]=[C:21]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:20]=1)=[C:8]([S:11]([CH3:14])(=[O:13])=[O:12])[C:7]([CH3:15])=[CH:6][CH:5]=2

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 807IodineHCID 3939Lithium HydroxideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 21077820HCID 21077820, compoundHCID 178527881HCID 178527881, compound

Product 1

HCID 10005028HCID 10005028, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of the product from step b) (200 mg) and iodine (210 mg) in DMF (2 ml) was treated with 2-thiazolethiol, 4-phenyl- (300 mg) and stirred for 1 hour. The solution was treated with 60% sodium hydride (4.0 molar equivalents) and stirred overnight. Methyl bromoacetate (0.30 g) was added followed after 30 minutes stirring by water (2 ml) tetrahydrofuran (2 ml) and lithium hydroxide (0.20 g). After stirring a further 30 minutes, the reaction mixture was acidified (2M HCl, 5 ml) and extracted into ethyl acetate (3×10 ml). The combined organics were washed with saturated brine (3×10 ml), dried (MgSO4) and evaporated. The residue was purified by reversed phase preparative HPLC to give the title compound (172 mg).

Workup

  1. stirringstirred overnight
  2. waitfollowed after 30 minutes
  3. stirringAfter stirring a further 30 minutes
  4. extractionextracted into ethyl acetate (3×10 ml)
  5. washThe combined organics were washed with saturated brine (3×10 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by reversed phase preparative HPLC

Sources & evidence

ORD record
ord-9d9ab17f50904fc899059383c28397b7
Source dataset
uspto-grants-2007_01
Patent number
US07166607B2

Reaction notes

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