Hydrochloric Acid → HCID 21310899, compound

HRID 583343Notes

Reaction equation

HRID 583343 reaction equation
[CH2:1]([N:8]([S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[C:9]1[C:17]([O:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:34](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35].[OH-].[Na+].Cl>CN(C=O)C.O.CCOC(C)=O>[CH2:1]([N:8]([S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[C:9]1[C:17]([O:18][CH2:19][CH2:20][CH2:21][O:22][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 28928tert-Butyldimethylsilyl chlorideHCID 21310898HCID 21310898, compound

Product 1

HCID 21310899HCID 21310899, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.145 g (0.308 mmol) of the product of Example 172 in 5.0 mL of DMF was added 0.105 g (1.539 mmol) of iidazle and 0.111 g (0.739 mmol) of t-butyidimethylsilyl chloride. The reaction was stirred at room temperature for 18 h and then 0.40 mL of 1N sodium hydroxide solution was added and the resulting mixture was sired for 1 h. The reaction mixture was then diluted with water, acidified with 5% HCl solution and extted with EtOAc. The combined organics were washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with EtOAc/Hexanes to provide 0.089 g (50%) of the desired product as a white foam. Electrospray Mass Spec: 586 (M+H).

Workup

  1. waitthe resulting mixture was sired for 1 h
  2. washThe combined organics were washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with EtOAc/Hexanes

Sources & evidence

ORD record
ord-96cee85f12f44dfa9227967099dd4c0f
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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