Triethylamine → HCID 59996369, compound

HRID 1814040Notes

Reaction equation

HRID 1814040 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N:6]([CH:9]1[CH:13]([OH:14])[CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]3=[O:31])=[CH:17][C:16]=2[F:32])[CH2:10]1)=[N+:7]=[N-:8].C(N(CC)CC)C>ClCCl>[N:6]([CH:9]1[CH:13]([O:14][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]3=[O:31])=[CH:17][C:16]=2[F:32])[CH2:10]1)=[N+:7]=[N-:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59996364HCID 59996364, compound

Product 1

HCID 59996369HCID 59996369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (8 μL, 0.10 mmol) was added to a solution of N-({(5S)-3-[4-(3-azido-4-hydroxypyrrolidin-1-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (30 mg, 0.08 mmol) and triethylamine (16 μL, 0.12 mmol) in dichloromethane (0.5 mL) at 0° C. After 1 h, the solution was diluted with more dichloromethane, washed with dilute NaHCO3, brine and dried (MgSO4), filtered and concentrated to give the title compound as an oil. This material was used directly in the next reaction.

Workup

  1. washwashed with dilute NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0a564a9be9a84fec88439c8461f4a3be
Source dataset
uspto-grants-2005_04
Patent number
US06875784B2

Reaction notes

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