Glycolic Acid → HCID 24885628, compound

HRID 750922Notes

Reaction equation

HRID 750922 reaction equation
[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@H:19]([CH2:21][NH2:22])[O:18][C:17]3=[O:23])=[CH:12][C:11]=2[F:24])[CH2:6][CH2:5]1)#[N:2].[C:25](O)(=[O:28])[CH2:26][OH:27].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@H:19]([CH2:21][NH:22][C:26](=[O:27])[CH2:25][OH:28])[O:18][C:17]3=[O:23])=[CH:12][C:11]=2[F:24])[CH2:6][CH2:5]1)#[N:2]

Participants

6

Reactant 3

HCID 757Glycolic AcidHCID 10868DicyclohexylcarbodiimideHCID 24885852HCID 24885852, compound

Product 1

HCID 24885628HCID 24885628, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The mixture of (S)-N-{3-[4-(4-cyanomethylidene-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-amine (2.87 mmol), glycolic acid (5.74 mmol), dicyclohexylcarbodiimide (7.17 mmol), 4-dimethylaminopyridine (100 mg) in dichloromethane (50 ml) was stirred for 3 hours. The reaction mixture was filtered. The filtrate was evaporated and the residue was purified by column chromatography over a silica gel to give title compound in 70% yield.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customThe filtrate was evaporated
  3. customthe residue was purified by column chromatography over a silica gel

Sources & evidence

ORD record
ord-a3f80c282a464328a7d2a6360516de4f
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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