Triethylamine → (S)-N-[[3-[3-fluoro-4-(1,2,3,4,6,7-hexahydro-5-oxo-1,4-diazepin-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide

HRID 609580Notes

Reaction equation

HRID 609580 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH2:22])[O:18][C:17]2=[O:23])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:14][CH2:13][C:12](=[O:15])[NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C.[C:31](SCC)(=[S:33])[CH3:32]>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:31](=[S:33])[CH3:32])[O:18][C:17]2=[O:23])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:14][CH2:13][C:12](=[O:15])[NH:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 70093Ethyl dithioacetate2×HCID 54468014HCID 54468014, compound

Product 1

HCID 9800011(S)-N-[[3-[3-fluoro-4-(1,2,3,4,6,7-hexahydro-5-oxo-1,4-diazepin-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 0.12 g of the product of Example 2, Step 2 and 0.40 mL of triethylamine in a mixture of methylene chloride (10 mL) and methanol (10 mL), under nitrogen, is treated with ethyl dithioacetate (0.05 mL) and kept at ambient temperature for 145 hours. Additional 0.05 m]L portions of ethyl dithioacetate are added after 24, 31 and 49 hours; additional triethylamine (1.0 mL) is also added after 49 hours. The mixture is concentrated to a small volume, diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and concentrated. Chromatography of the residue on silica gel with 3.5% methanol-methylene chloride gave 0.061 g of the titled product.

Workup

  1. concentrationThe mixture is concentrated to a small volume
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea189cdb23324f33bbb9a2e1773cabfb
Source dataset
uspto-grants-1999_12
Patent number
US05998406

Reaction notes

Loading…