2-Methoxyethyl chloroformate → HCID 69365571, compound

HRID 723764Notes

Reaction equation

HRID 723764 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]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])[CH2:4]1.C(=O)(O)[O-].[Na+].Cl[C:33]([O:35][CH2:36][CH2:37][O:38][CH3:39])=[O:34]>ClCCl>[CH3:39][O:38][CH2:37][CH2:36][O:35][C:33]([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]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])[CH2:4]1)=[O:34]

Participants

5

Reactant 3

HCID 694002-Methoxyethyl chloroformateHCID 516892Sodium BicarbonateHCID 69363912HCID 69363912, compound

Product 1

HCID 69365571HCID 69365571, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5R)-3-(4-((3R)-3-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride (200 mg, 0.52 mM) was suspended by stirring in dichloromethane (10 ml) at 0° and sodium bicarbonate solution (5 ml) added. 2-Methoxyethyl chloroformate (340 mg, 2.46 mM) was added, and the mixture stirred 4 hours, allowing the temperature to rise to ambient. The organic layer was separated, washed with sodium dihydrogen phosphate (2%, 2×15 ml), water (15 ml) and dried (magnesium sulfate). Filtration and evaporation gave the desired product (183 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with sodium dihydrogen phosphate (2%, 2×15 ml), water (15 ml)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-c57827052e5d4fef94b9d81d271a8980
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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