Formic Acid → HCID 54427415, compound

HRID 428768Notes

Reaction equation

HRID 428768 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3([F:19])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[C:9]([F:20])[CH:8]=2)[CH2:5][C@H:4]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:3]1.Cl.CN(C)CCCN=C=NCC.[CH:38](O)=[O:39]>O1CCCC1.O.C(Cl)Cl>[CH:38]([N:16]1[CH2:17][CH2:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([N:6]3[CH2:5][C@H:4]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:3][C:2]3=[O:1])=[CH:8][C:9]=2[F:20])([F:19])[CH2:14][CH2:15]1)=[O:39]

Participants

7

Reactant 3

HCID 284Formic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54376127HCID 54376127, compound

Product 1

HCID 54427415HCID 54427415, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-3-N-[[2-oxo-3-[4-(4-fluoro-4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 74, Step 5, 205 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (145 mg) and formic acid (28 μL) in dry tetrahydrofuran (11.6 mL) is diluted with water to solubilize all reactants and stirred at ambient temperature for 6 hrs. The reaction is then diluted with methylene chloride (30 mL), washed with water (20 mL) and saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue is chromatographed on silica gel (230-400 mesh, 40 g), eluting with a gradient of methanol/methylene chloride (3/97-5/95). Those fractions with an Rf=0.40 by TLC (methanol/chloroform, 10/90) are pooled and concentrated and the residue is recrystallized from chloroform/diethyl ether to give the title compound, mp 180-181° C. (decomp.).

Workup

  1. washwashed with water (20 mL) and saline (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is chromatographed on silica gel (230-400 mesh, 40 g)
  5. washeluting with a gradient of methanol/methylene chloride (3/97-5/95)
  6. concentrationconcentrated
  7. customthe residue is recrystallized from chloroform/diethyl ether

Sources & evidence

ORD record
ord-064394b70e6945b98775c43734d2bacc
Source dataset
uspto-grants-2001_11
Patent number
US06313307B1

Reaction notes

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