Pyridine → HCID 42598818, compound

HRID 875261Notes

Reaction equation

HRID 875261 reaction equation
[OH:1][C:2]1([CH2:19][OH:20])[C:6](=[O:7])[O:5][C@H:4]2[C:8]3[C@@:13]([CH3:16])([CH2:14][CH2:15][C:3]12[OH:18])[CH2:12][CH2:11][CH2:10][C:9]=3[CH3:17].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22].N1C=CC=CC=1>ClCCl.CN(C1C=CN=CC=1)C>[CH3:28][C:27]1[CH:29]=[CH:30][C:24]([S:21]([O:20][CH2:19][C:2]2([OH:1])[C:6](=[O:7])[O:5][C@H:4]3[C:8]4[C@@:13]([CH3:16])([CH2:14][CH2:15][C:3]23[OH:18])[CH2:12][CH2:11][CH2:10][C:9]=4[CH3:17])(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 42598580HCID 42598580, compound

Product 1

HCID 42598818HCID 42598818, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Compound of example 2 (126.6 mg, 0.449 mmol) was dissolved in dichloromethane (5 mL). Tosyl chloride (427.9 mg, 2.24 mmole), pyridine (355.05 mg, 4.48 mmole) and DMAP (2 mg) were added to this solution and reaction mixture was stirred for 72 hours. Reaction mixture was extracted with dichloromethane (5 mL). Dichloromethane was removed and crude product was purified by column chromatography (silica gel, 5-10% ethyl acetate in petroleum ether) to obtain the title compound.

Workup

  1. customReaction mixture
  2. extractionwas extracted with dichloromethane (5 mL)
  3. customDichloromethane was removed
  4. customcrude product was purified by column chromatography (silica gel, 5-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-259e9cc557374a549570abcbb8af1a7d
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

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