Triethylamine → HCID 59996393, compound

HRID 1814042Notes

Reaction equation

HRID 1814042 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[CH:7]12[NH:12][CH:11]1[CH2:10][N:9]([C:13]1[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]3=[O:29])=[CH:15][C:14]=1[F:30])[CH2:8]2.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][CH2:3][C:4]([N:12]1[CH:11]2[CH:7]1[CH2:8][N:9]([C:13]1[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]3=[O:29])=[CH:15][C:14]=1[F:30])[CH2:10]2)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 59996350HCID 59996350, compound

Product 1

HCID 59996393HCID 59996393, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methoxyacetyl chloride (6 mL, 0.067 mmol) was added to a cooled (0° C.) solution of N-({(5S)-3-[4-(3,6-diazabicyclo[3.1.0]hex-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (15 mg, 0.05 mmol) in triethylamine (14 μL, 0.10 mmol) and dichloromethane (1.0 mL). After 1 hour, the solution was diluted with dichloromethane, and washed with dilute NaHCO3, brine, and dried (MgSO4), filtered and concentrated. Purification by pTLC (5% MeOH—CH2Cl2) provided the title compound.

Workup

  1. washwashed with dilute NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by pTLC (5% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-41148a8f965e49c2a98bece5890dc2bd
Source dataset
uspto-grants-2005_04
Patent number
US06875784B2

Reaction notes

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