Methyl chloroformate → HCID 69363935, compound

HRID 723760Notes

Reaction equation

HRID 723760 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][CH3:36])=[O:34]>ClCCl>[CH3:36][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 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 69363912HCID 69363912, compound

Product 1

HCID 69363935HCID 69363935, compoundYield 67.7%

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, 0.5 mM) in dichloromethane (20 ml) was cooled to 0° and treated with 5% sodium bicarbonate solution (5 ml). The resulting suspension was stirred vigorously, methyl chloroformate (245 mg, 2.6 mM) added, and stirring continued for 3 hours at ambient temperature. The organic layer was separated, washed with 2% sodium dihydrogen phosphate (2×10 ml), brine (10 ml), and dried (magnesium sulfate), to give the desired product (143 mg).

Workup

  1. stirringstirring
  2. customThe organic layer was separated
  3. washwashed with 2% sodium dihydrogen phosphate (2×10 ml), brine (10 ml)
  4. dry with materialdried (magnesium sulfate)

Sources & evidence

ORD record
ord-22f8c7099cb74b48bddc8a39b6403799
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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