Triethylamine → HCID 9798338, compound

HRID 1935618Notes

Reaction equation

HRID 1935618 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:11]3[CH2:15][C@H:14]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])[O:13][C:12]3=[O:21])[CH:8]=2)[NH:3]1.C(N(CC)CC)C.C([O:32][CH2:33][C:34](Cl)=[O:35])(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CO>[C:33]([N:3]1[C:4]2[C:9](=[CH:8][C:7]([N:11]3[CH2:15][C@H:14]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])[O:13][C:12]3=[O:21])=[CH:6][CH:5]=2)[CH2:10][CH:2]1[CH3:1])(=[O:32])[CH2:34][OH:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 26297Acetoxyacetyl chlorideHCID 12971627HCID 12971627, compound

Product 1

HCID 9798338HCID 9798338, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent4×

Procedure

The deprotected material N-{[(5S)-3-(2-methyl-2,3-dihydro-1H-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (0.48 g, 1.66 mmol) (EXAMPLE 1, Step 6) and triethylamine (0.35 mL, 2.5 mmol) are dissolved in CH2Cl2 (10 mL). Acetoxyacetylchloride (0.233 mL, 2.16 mmol) is added along with additional CH2Cl2 (25 mL). After 20 minutes the mixture is diluted with CH2Cl2 (200 mL) and washed with water, brine and dried (Na2SO4). Removal of solvent gave a residue that is dissolved in MeOH (20 mL) and CH2Cl2 (80 mL). Potassium carbonate (200 mg) is added and the reaction is stirred for 20 minutes and evaporated to dryness. The residue is purified on silica gel with 2% MeOH/CH2Cl2 to give 0.5 g (86%) of an off white solid: mp 130-133° C.; HRMS (FAB) calcd for C17H21N3O5+H1 348.1559, found 348.1569.Anal. Calcd for C17H21N3O5: C, 58.78; H, 6.09; N, 12.10.Found: C, 58.60; H, 6.27; N, 11.53.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (Na2SO4)
  3. customRemoval of solvent
  4. customgave a residue that
  5. customevaporated to dryness
  6. customThe residue is purified on silica gel with 2% MeOH/CH2Cl2
  7. customto give 0.5 g (86%) of an off white solid

Sources & evidence

ORD record
ord-b2e4af2d43554f8faf8109406b017676
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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