Dicyclohexylcarbodiimide → HCID 70000079, compound

HRID 1167434Notes

Reaction equation

HRID 1167434 reaction equation
CC1(C)[O:6][C@@H:5]([C:7](O)=[O:8])[CH2:4][O:3]1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.Cl.[N:47]1([C:53]2[CH:58]=[CH:57][C:56]([N:59]3[CH2:63][C@H:62]([CH2:64][O:65][C:66]4[CH:70]=[CH:69][O:68][N:67]=4)[O:61][C:60]3=[O:71])=[CH:55][C:54]=2[F:72])[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1>ClCCl>[OH:6][C@H:5]([CH2:7][OH:8])[C:4]([N:50]1[CH2:49][CH2:48][N:47]([C:53]2[CH:58]=[CH:57][C:56]([N:59]3[CH2:63][C@H:62]([CH2:64][O:65][C:66]4[CH:70]=[CH:69][O:68][N:67]=4)[O:61][C:60]3=[O:71])=[CH:55][C:54]=2[F:72])[CH2:52][CH2:51]1)=[O:3]

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10855606(4R)-2,2-Dimethyl-1,3-dioxolane-4-carboxylic acidHCID 69980303HCID 69980303, compound

Product 1

HCID 70000079HCID 70000079, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2-dimethyl-1,3-dioxolane-4(R)-carboxylic acid (162 mg, 1.1 mmol) in dichloromethane (20 ml) under nitrogen was cooled with stirring to 4°, and treated successively with dicyclohexylcarbodiimide (227 mg, 1.1 mmol) and 1-hydroxybenzotriazole (147 mg, 1.1 mmol), then stirred at the same temperature for 1 hour. N,N-Diisopropylethylamine (129 mg, 1 mmol) was added, followed by 3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one dihydrochloride (399 mg, 0.92 mmol). The mixture was stirred for 2 hours, allowing the temperature to rise to ambient. Solid was filtered off, and the organic solution washed with water (2×20 ml), dried over magnesium sulfate and evaporated to dryness. The residue was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 10% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (82 mg).

Workup

  1. stirringstirred at the same temperature for 1 hour
  2. stirringThe mixture was stirred for 2 hours
  3. filtrationSolid was filtered off
  4. washthe organic solution washed with water (2×20 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
  8. washeluting with
  9. temperaturea gradient increasing in polarity from 0 to 10% MeOH in dichloromethane
  10. customevaporated

Sources & evidence

ORD record
ord-8095d34f590846269f5d088013e5dae1
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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