Formic Acid → HCID 76652336, compound

HRID 1666944Notes

Reaction equation

HRID 1666944 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[CH2:11]([CH:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:41])[CH:25]([CH2:35][CH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1)[CH2:26][NH:27][O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[CH2:11]([CH:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:41])[CH:25]([CH2:35][CH:36]1[CH2:37][CH2:38][CH2:39][CH2:40]1)[CH2:26][N:27]([O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1)[CH:1]=[O:2])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 76652338HCID 76652338, compound

Product 1

HCID 76652336HCID 76652336, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of formic acid (45.0 mL, 1193 mmol) and acetic anhydride (90.0 mL, 952 mmol) is stirred at 50° C. for one hour under nitrogen. A second flask is charged with 4-benzyl-3-[2-cyclopentylmethyl-3-(tetrahydro-pyran-2-yloxyamino)-propionyl]-oxazolidin-2-one (21.62 g, 50.2 mmol), Et3N (170.0 mL, 1220 mmol), and anhydrous DCM (450 mL). This second mixture is cooled to 4° C. under nitrogen, and the mixed acid solution is slowly added to the second flask, while maintaining 10° C. The combined mixture is stirred for 30 minutes at 10° C., quenched with saturated, washed with aqueous NaHCO3 solution, and extracted with DCM. The DCM layers are combined, dried over Na2SO4, and concentrated. The crude product is purified by flash chromatography (SiO2, 50% EtOAc in hexane), which gives N-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-2-cyclopentylmethyl-3-oxo-propyl]-N-(tetrahydro-pyran-2-yloxy)-formamide (20.10 g, 87% yield) as an oil.

Workup

  1. temperatureThis second mixture is cooled to 4° C. under nitrogen
  2. additionthe mixed acid solution is slowly added to the second flask
  3. temperaturewhile maintaining 10° C
  4. stirringThe combined mixture is stirred for 30 minutes at 10° C.
  5. customquenched with saturated,
  6. washwashed with aqueous NaHCO3 solution
  7. extractionextracted with DCM
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe crude product is purified by flash chromatography (SiO2, 50% EtOAc in hexane), which

Sources & evidence

ORD record
ord-4762b0027ac64c498f64d13814388e20
Source dataset
uspto-grants-2011_10
Patent number
US08044199B2

Reaction notes

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