Ammonia → HCID 60018003, compound

HRID 723889Notes

Reaction equation

HRID 723889 reaction equation
[N:1]1([C:6]2[C:11]([F:12])=[CH:10][C:9]([N:13]3[CH2:17][C@H:16]([C:18]([O:20]C)=O)[O:15][C:14]3=[O:22])=[CH:8][C:7]=2[F:23])[CH2:5][CH:4]=[CH:3][CH2:2]1.[NH3:24]>CO>[N:1]1([C:6]2[C:11]([F:12])=[CH:10][C:9]([N:13]3[CH2:17][C@H:16]([C:18]([NH2:24])=[O:20])[O:15][C:14]3=[O:22])=[CH:8][C:7]=2[F:23])[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68489834HCID 68489834, compound

Product 1

HCID 60018003HCID 60018003, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (5R)-3-[4-(2,5-dihydro-1H-pyrrol-1-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidine-5-carboxylate (Step 4, 0.09 g, 0.28 mmol) in 2.0M ammonia in MeOH (2.8 mL) is heated to 55° C. for 4 h. The reaction mixture is cooled, concentrated and the residue purified by pTLC (5% MeOH/CH2Cl2) to give the title compound (50 mg, 58%); MS for C14H13F2N3O3MS m/z 310.5 (M+H)+; 1H NMR (300 MHz, d6-DMSO): δ 3.93–3.98 (m, 1H), 4.17–4.25 (m, 5H), 4.97–5.02 (m, 1H), 5.93 (s, 2H), 7.27 (d, 2H), 7.61 (s, 1H), 7.85 (s, 1H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated
  3. customthe residue purified by pTLC (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3df3f78b08c9418bb78821e4e15fb44c
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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