Hydrochloric Acid → HCID 10127215, compound

HRID 1268983Notes

Reaction equation

HRID 1268983 reaction equation
[O:1]=[S:2]1(=[O:34])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([CH2:25][C:26]#[C:27][Si](C)(C)C)[N:22]=[N:21]4)[O:16][C:15]3=[O:32])=[CH:10][C:9]=2[F:33])[CH2:4][CH2:3]1.[OH-].[K+].Cl>CO>[O:34]=[S:2]1(=[O:1])[CH2:3][CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([CH2:25][C:26]#[CH:27])[N:22]=[N:21]4)[O:16][C:15]3=[O:32])=[CH:10][C:9]=2[F:33])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18447027HCID 18447027, compound2×

Product 1

HCID 10127215HCID 10127215, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-(3-(trimethylsilyl)-2-propynyl)-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (251 mg, 0.5 mmol) (Intermediate 5) was dissolved in methanol (10 ml). Potassium hydroxide (1 M, 0.75 ml) was added and the mixture was stirred at room temperature for 4 hours. Aqueous HCl (2M, 0.5 ml) was added, the excess of methanol was evaporated and the residue was extracted with dichloromethane, dried over magnesium sulfate and concentrated to give the title product (220 mg).

Workup

  1. customthe excess of methanol was evaporated
  2. extractionthe residue was extracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2dd30c8105774649902aef42f08a2465
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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