Dichloroacetic Acid → HCID 60133556, compound

HRID 2247068Notes

Reaction equation

HRID 2247068 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][NH2:23])[O:19][C:18]4=[O:24])=[CH:13][C:12]=3[F:25])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[Cl:26][CH:27]([Cl:31])[C:28](O)=[O:29].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[O:1]1[C:5]2([CH2:6][CH2:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][NH:23][C:28](=[O:29])[CH:27]([Cl:31])[Cl:26])[O:19][C:18]4=[O:24])=[CH:13][C:12]=3[F:25])[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6597Dichloroacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 60133549HCID 60133549, compound

Product 1

HCID 60133556HCID 60133556, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by reacting (S)-N-{3-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-amine (0.2 mmol, Example H) with dichloroacetic acid (2.1 mmol), dicyclohexylcarbodimide (2.1 mmol) in dichloromethane (10 ml) at a temperature 0-25° C. for 3 hours followed by silica gel column chromatographic purification in 52% yield.

Workup

  1. customat a temperature 0-25° C.
  2. customfor 3 hours
  3. customfollowed by silica gel column chromatographic purification in 52% yield

Sources & evidence

ORD record
ord-ff794637b42d441b9a201ef949720426
Source dataset
uspto-grants-2010_03
Patent number
US07687627B2

Reaction notes

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