Sodium hydride → HCID 10217848, compound

HRID 1268972Notes

Reaction equation

HRID 1268972 reaction equation
[O:1]=[S:2]1(=[O:45])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([CH2:25]OP(OC5C=CC=CC=5)(OC5C=CC=CC=5)=O)[N:22]=[N:21]4)[O:16][C:15]3=[O:43])=[CH:10][C:9]=2[F:44])[CH2:4][CH2:3]1.[SH:46][C:47]1[NH:48][CH:49]=[CH:50][N:51]=1.[H-].[Na+]>CN(C=O)C>[O:45]=[S:2]1(=[O:1])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([CH2:25][S:46][C:47]5[NH:48][CH:49]=[CH:50][N:51]=5)[N:22]=[N:21]4)[O:16][C:15]3=[O:43])=[CH:10][C:9]=2[F:44])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10312499HCID 10312499, compoundHCID 178527877HCID 178527877, compound

Product 1

HCID 10217848HCID 10217848, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-[(diphenoxyphosphinyl)oxymethyl]-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 15) (0.125 g, 0.19 mmol) was added to a solution of 2-mercaptoimidazole (38 mg, 0.38 mmol) in DMF (2 ml) and the resulting solution was added to a suspension of sodium hydride (15 mg, 0.38 mmol) in DMF (2 ml). The reaction mixture was stirred for 30 minutes and then quenched with excess of aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate, was washed with sodium bicarbonate, water and brine, dried over sodium sulfate and concentrated in vacuo to give 40 mg (42%) of the title compound as a colourless solid.

Workup

  1. customquenched with excess of aqueous sodium bicarbonate
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwas washed with sodium bicarbonate, water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-012ab258d52140a1910f1dcb2b9b0fea
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

Loading…