Hydrochloric Acid → HCID 178520515, compound

HRID 1167443Notes

Reaction equation

HRID 1167443 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([N:29]5[CH2:33][C@H:32]([CH2:34][O:35][C:36]6[CH:40]=[CH:39][O:38][N:37]=6)[O:31][C:30]5=[O:41])=[CH:25][C:24]=4[F:42])[CH2:19][CH2:18]3)=[O:16])[N:10]=[CH:9]2)C=CC=CC=1.Cl.C(N(CC)CC)C>C(O)C.CO>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][C@H:32]([CH2:34][O:35][C:36]5[CH:40]=[CH:39][O:38][N:37]=5)[O:31][C:30]4=[O:41])=[CH:25][C:24]=3[F:42])[CH2:19][CH2:18]2)=[O:16])[N:10]=[CH:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 699799123-(4-(4-(3-(1-Triphenylmethyl-4-imidazolyl)propanoyl)-piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one

Product 1

HCID 178520515HCID 178520515, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

3-(4-(4-(3-(1-Triphenylmethyl-4-imidazolyl)propanoyl)-piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (460 mg, 0.63 mmol), was dissolved in a mixture of ethanol (20 ml) and MeOH (10 ml), cooled to 0° and treated with a solution of hydrogen chloride in ethanol (3.8 M, 5 ml). After stirring 48 hours at ambient temperature, the pH was adjusted to 8 with triethylamine, and the mixture evaporated to dryness. The residue was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient from 0 to 20% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (60 mg). MS (ESP): 485 (MH+) for C23H25FN6O5;

Workup

  1. temperaturecooled to 0°
  2. customthe mixture evaporated to dryness
  3. customThe residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
  4. washeluting with a gradient from 0 to 20% MeOH in dichloromethane
  5. customevaporated

Sources & evidence

ORD record
ord-c6962f781de24284b64ef29103120b47
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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