Dichloromethane → 3-(4-(3(S)-Acetamidopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloro-ethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

HRID 8163Notes

Reaction equation

HRID 8163 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]([C:29]4[CH:33]=[CH:32][O:31][N:30]=4)[C:21]([O:23][CH2:24][C:25]([Cl:28])([Cl:27])[Cl:26])=[O:22])[O:16][C:15]3=[O:34])=[CH:10][C:9]=2[F:35])[CH2:4]1.C(=O)(O)[O-].[Na+].ClCCl.[C:44](OC(=O)C)(=[O:46])[CH3:45]>O>[C:44]([NH:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]([C:29]4[CH:33]=[CH:32][O:31][N:30]=4)[C:21]([O:23][CH2:24][C:25]([Cl:28])([Cl:26])[Cl:27])=[O:22])[O:16][C:15]3=[O:34])=[CH:10][C:9]=2[F:35])[CH2:4]1)(=[O:46])[CH3:45]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2×HCID 516892Sodium BicarbonateHCID 695849253-(4(3(S) aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt

Product 1

HCID 695847253-(4-(3(S)-Acetamidopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloro-ethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-oneYield 83.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyl-oxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (400 mg, 0.74 mM) was dissolved in water (5 ml) and treated with aqueous sodium bicarbonate solution (5 ml) and dichloromethane (10 ml) in an ice-bath. Acetic anhydride (216 mg, 2 mM) was added, the mixture stirred 18 hours, allowing the temperature to rise to ambient, followed by addition of a further portion of acetic anhydride (216 mg), and a further period of 10 hours stirring. The organic phase was separated, washed with aqueous sodium dihydrogen phosphate (2%, 2×15 ml), brine (10 ml), and dried (magnesium sulfate). Evaporation gave the desired product (338 mg).

Workup

  1. stirringa further period of 10 hours stirring
  2. customThe organic phase was separated
  3. washwashed with aqueous sodium dihydrogen phosphate (2%, 2×15 ml), brine (10 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customEvaporation

Sources & evidence

ORD record
ord-193fe8c4c29b49618063ab36b76ee128
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Reaction notes

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