Ethanol → HCID 89622450, compound

HRID 1500818Notes

Reaction equation

HRID 1500818 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:21]3[S:22][C:23]4[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH3:32])=[CH:26][C:24]=4[CH:25]=3)[C:9]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]3)=[C:10]([CH2:11][OH:12])[N:6]2[N:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.[CH2:37](O)[CH3:38].CC[O-].[Na+]>ClCCl>[NH2:1][C:2]1[C:7]2=[C:8]([C:21]3[S:22][C:23]4[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH3:32])=[CH:26][C:24]=4[CH:25]=3)[C:9]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]3)=[C:10]([CH2:11][O:12][CH2:37][CH3:38])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2723922Sodium ethoxideHCID 89622338HCID 89622338, compound

Product 1

HCID 89622450HCID 89622450, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of Example 125 (100 mg, 221 μmol) in dichloromethane (10 ml) was treated with thionyl chloride (161 μl, 2.21 mmol), and the mixture was stirred at rt for 30 min. Ethanol was added, and the volatiles were evaporated under reduced pressure. The residue was dissolved in ethanol (10 ml), sodium ethylate (30 mg, 442 μmol) was added, and the mixture was stirred at rt for 1 h. The mixture was then directly separated by preparative RP-HPLC (Reprosil C18, gradient 20-40% acetonitrile/0.2% aq. trifluoroacetic acid). The product fractions were combined and alkalized by addition of sat. aq. sodium bicarbonate solution. The solution was extracted with ethyl acetate, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated to yield 57 mg of the title compound (54% of th.).

Workup

  1. customthe volatiles were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethanol (10 ml)
  3. stirringthe mixture was stirred at rt for 1 h
  4. customThe mixture was then directly separated by preparative RP-HPLC (Reprosil C18, gradient 20-40% acetonitrile/0.2% aq. trifluoroacetic acid)
  5. additionalkalized by addition of sat. aq. sodium bicarbonate solution
  6. extractionThe solution was extracted with ethyl acetate
  7. washthe organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-281b5264f7174242b3ec8c789ebee48a
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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