Hydrochloric Acid → HCID 24997807, compound

HRID 1024119Notes

Reaction equation

HRID 1024119 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH:15]=[C:14]2[C:18]2[CH:23]=[CH:22][C:21]([C@H:24]([O:30]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:20][CH:19]=2)=[CH:8][CH:9]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].C1COCC1.Cl>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH:15]=[C:14]2[C:18]2[CH:19]=[CH:20][C:21]([C@H:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:22][CH:23]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 68702128HCID 68702128, compound

Product 1

HCID 24997807HCID 24997807, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 45 (40 mg, 0.069 mmol), K2CO3 (10 mg, 0.072 mmol) in methanol (0.5 mL) was stirred at room temperature. After 1 h, the diester had not dissolved and so 0.2 mL THF was added. The reaction was stirred further for 1.5 h and then 10 mL 1 M HCl was added. The mixture was extracted with ethyl acetate (2×20 mL) and the combined solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography using a Combiflash unit by Teledyne Isco (12 g silica gel, 0%→20% ethyl acetate/hexanes) gave the title compound (22 mg, 0.051 mmol, 75%).

Workup

  1. stirringThe reaction was stirred further for 1.5 h
  2. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  3. dry with materialthe combined solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-c258559040a649649c2cdd8c9a49a023
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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