Diisopropylethylamine → (5R)-3-[3,5-Difluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

HRID 1452601Notes

Reaction equation

HRID 1452601 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([N:21]3[CH2:25][C@H:24]([CH2:26][N:27]4[CH:31]=[C:30]([CH3:32])[N:29]=[N:28]4)[O:23][C:22]3=[O:33])=[CH:16][C:15]=2[F:34])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.ClC(OC(Cl)=O)C>ClCCl>[F:34][C:15]1[CH:16]=[C:17]([N:21]2[CH2:25][C@H:24]([CH2:26][N:27]3[CH:31]=[C:30]([CH3:32])[N:29]=[N:28]3)[O:23][C:22]2=[O:33])[CH:18]=[C:19]([F:20])[C:14]=1[C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 10367222(5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

Product 1

HCID 57526986(5R)-3-[3,5-Difluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (Example 39) (1.74 g, 3.74 mmol) was dissolved in dichloromethane (20 ml) and cooled to 0° C. Diisopropylethylamine (0.13 ml, 0.75 mmol) was added, followed by addition of 1-chloroethylchloroformate (0.48 ml, 4.48 mmol). It was stirred for 30 minutes, then allowed to warm to room temperature. After 16 hours, the reaction mixture was concentrated under vacuum. The intermediate chloroethylcarbamate was dissolved in methanol (20 ml) and heated to reflux. After 30 min, the reaction mixture was cooled to room temperature and concentrated under vacuum to give the title compound as the hydrochloride salt (1.5 g), which was used without further purification.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 16 hours
  3. concentrationthe reaction mixture was concentrated under vacuum
  4. dissolutionThe intermediate chloroethylcarbamate was dissolved in methanol (20 ml)
  5. temperatureheated to reflux
  6. waitAfter 30 min
  7. temperaturethe reaction mixture was cooled to room temperature
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dedc02bd80da45338214db8880b653f5
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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