Hydrochloric Acid → HCID 58182904, compound

HRID 2063733Notes

Reaction equation

HRID 2063733 reaction equation
Cl.[C:2]1([S:8]([N:11]2[C:23]3[CH2:22][N:21]([CH2:24][CH:25]([CH:34]4[CH2:39][CH2:38][C:37]([N:47]([CH3:49])[CH3:48])([C:40]5[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=5)[CH2:36][CH2:35]4)[O:26][Si](C(C)(C)C)(C)C)[CH2:20][CH2:19][C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[C:2]1([S:8]([N:11]2[C:23]3[CH2:22][N:21]([CH2:24][CH:25]([CH:34]4[CH2:35][CH2:36][C:37]([N:47]([CH3:49])[CH3:48])([C:40]5[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=5)[CH2:38][CH2:39]4)[OH:26])[CH2:20][CH2:19][C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)(=[O:9])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69812763HCID 69812763, compound

Product 1

HCID 58182904HCID 58182904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 M hydrochloric acid (20 ml) was added to a solution of the product from stage 8 (176 mg, 0.255 mmol) in tetrahydrofuran (20 ml) and the mixture was stirred at room temperature for 1 d. The reaction mixture was then stirred at 50° C. for 15 h and then at room temperature for a further 16 h. The mixture was then rendered alkaline with 2 M sodium hydroxide solution (30 ml) and the phases were separated. The aqueous phase was extracted with diethyl ether (3×10 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product 151 mg) was purified by flash chromatography with methylene chloride/methanol (97:3).

Workup

  1. stirringThe reaction mixture was then stirred at 50° C. for 15 h
  2. waitat room temperature for a further 16 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with diethyl ether (3×10 ml)
  5. dry with materialThe combined organic phases were dried with sodium sulfate
  6. concentrationconcentrated i
  7. customThe crude product 151 mg) was purified by flash chromatography with methylene chloride/methanol (97:3)

Sources & evidence

ORD record
ord-215259afdf9f406db30b65f9f490d0de
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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