Methanesulfonyl chloride → HCID 86592848, compound

HRID 2212188Notes

Reaction equation

HRID 2212188 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH:17]([CH2:19][OH:20])[CH2:16][CH:15]([N:21]2[C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:31])[C:25]=3[C:24]3=[N:32][O:33][C:34]([CH3:35])=[C:23]3[C:22]2=[O:36])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH:17]([CH2:19][O:20][S:1]([CH3:4])(=[O:3])=[O:2])[CH2:16][CH:15]([N:21]2[C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:31])[C:25]=3[C:24]3=[N:32][O:33][C:34]([CH3:35])=[C:23]3[C:22]2=[O:36])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69652385HCID 69652385, compound

Product 1

HCID 86592848HCID 86592848, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Add DMAP (5 mg, cat.) and mesyl chloride (0.2 mL, 2.5 mmol) to a solution of 3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-5-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (0.95 g, 2.1 mmol) in pyridine (10 mL). Stir overnight at room temperature then concentrate to dryness. Partition between EtOAc, and water. Extract 2× with EtOAc. Wash the combined organics 3× with brine, dry over Na2SO4, filter and concentrate to dryness to afford the title compound (0.87 g, 79%) as a white solid as a mixture of cis isomers. MS(IS) 526.0 (M+); TLC (50% EtOAc/hexanes) Rf=0.65.

Workup

  1. concentrationthen concentrate to dryness
  2. customPartition between EtOAc, and water
  3. extractionExtract 2× with EtOAc
  4. washWash the combined organics 3× with brine
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-26b8b2d4fcdb46c2a7b877281a8e26d3
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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