1,1'-Carbonyldiimidazole → HCID 53880492, compound

HRID 277798Notes

Reaction equation

HRID 277798 reaction equation
[O:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=[N:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[O:21]=[C:22]1[N:26]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[C:29]([F:39])[CH:28]=2)[CH2:25][C@H:24]([CH2:40][NH:41][C:42](=[O:44])[CH3:43])[O:23]1>O1CCCC1>[O:1]1[C:5]([C:6]([N:36]2[CH2:37][CH2:38][CH:33]([C:30]3[CH:31]=[CH:32][C:27]([N:26]4[CH2:25][C@H:24]([CH2:40][NH:41][C:42](=[O:44])[CH3:43])[O:23][C:22]4=[O:21])=[CH:28][C:29]=3[F:39])[CH2:34][CH2:35]2)=[O:8])=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 20605991,2-Oxazole-5-carboxylic acidHCID 15887422(S)-(-)-N-[[2-Oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 53880492HCID 53880492, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of isoxazole-5-carboxylic acid (79 mg) and 1,1′-carbonyldiimidazole (80 mg) in dry tetrahydrofuran (2.0 mL) is stirred at ambient temperature for one hour, and a solution of (S)-(−)-N-[[2-oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 20, 150 mg) in dry tetrahydrofuran (6.0 mL) is added. The mixture is then stirred at ambient temperature for 19 hours, concentrated under reduced pressure, diluted with methylene chloride (20 mL), washed with saturated aqueous sodium bicarbonate (10 mL), water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which is chromagraphed on silica gel (70-230 mesh, 10 g), eluting with methanol/methylene chloride (7.5/92.5). Pooling and concentration of those fractions with an Rf=0.67 by TLC (methanol/chloroform, 10/90) and recrystallization from chloroforr/diethyl ether gives the title compound, mp 290-292° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with methylene chloride (20 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (10 mL), water (10 mL) and saline (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product which
  7. washeluting with methanol/methylene chloride (7.5/92.5)
  8. customPooling and concentration of those fractions with an Rf=0.67 by TLC (methanol/chloroform, 10/90) and recrystallization from chloroforr/diethyl ether

Sources & evidence

ORD record
ord-40cf709a0c73435a9a8b1e41df43a113
Source dataset
uspto-grants-2002_03
Patent number
US06358942B1

Reaction notes

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