Triethylamine → HCID 54540060, compound

HRID 1167435Notes

Reaction equation

HRID 1167435 reaction equation
Cl.Cl.[N:3]1([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][O:21][C:22]4[CH:26]=[CH:25][O:24][N:23]=4)[O:17][C:16]3=[O:27])=[CH:11][C:10]=2[F:28])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][C:45](Cl)=[O:46]>N1C=CC=CC=1>[CH3:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][C:45]([N:6]1[CH2:5][CH2:4][N:3]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][O:21][C:22]4[CH:26]=[CH:25][O:24][N:23]=4)[O:17][C:16]3=[O:27])=[CH:11][C:10]=2[F:28])[CH2:8][CH2:7]1)=[O:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27595712-[2-(2-Methoxyethoxy)ethoxy]acetyl chlorideHCID 69980303HCID 69980303, compound

Product 1

HCID 54540060HCID 54540060, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)-oxazolidin-2-one dihydrochloride (399 mg, 0.92 mmol) in pyridine (10 ml) was added triethylamine (0.31 ml, 2.2 mmol) and 2-(2-(2-methoxyethoxy)ethoxy)acetyl chloride (197 mg, 1 mmol). The mixture was stirred for 18 hours, evaporated to dryness, the residue dissolved in dichloromethane, and 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 (95 mg).

Workup

  1. customevaporated to dryness
  2. dissolutionthe residue dissolved in dichloromethane
  3. custompurified by chromatography on a 10 g silica Mega Bond Elut® column
  4. washeluting with
  5. temperaturea gradient increasing in polarity from 0 to 10% MeOH in dichloromethane
  6. customevaporated

Sources & evidence

ORD record
ord-af03c71504874103841bcc53b1831711
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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