4-Toluenesulfonyl chloride → HCID 15528413, compound

HRID 712791Notes

Reaction equation

HRID 712791 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[NH2:7][CH:8]([CH2:11][CH:12]=[CH2:13])[CH2:9][OH:10].CCOC(C)=O.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>O.CCOC(C)=O.C1COCC1>[OH:10][CH2:9][CH:8]([NH:7][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27])[CH2:11][CH:12]=[CH2:13]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl Acetate2×HCID 10340Sodium CarbonateHCID 20064163HCID 20064163, compound

Product 1

HCID 15528413HCID 15528413, compoundYield 31.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

A solution of Na2CO3 (9.22 g, 86.92 mmol) in water (50 ml) was left under stirring at RT for 20 min prior addition of 2-aminopent-4-en-1-ol (D7) (8.3 g) and EtOAc (160 ml). After 30 minutes stirring, a solution of p-toluenesulfonyl chloride (12.9 g, 67.85 mmol) in EtOAc/THF (24/24 ml) was added over 15 minutes. The reaction mixture was stirred at RT for a weekend. Water (30 ml) and EtOAc (100 ml) were added to the reaction mixture, the phases were separated and the aqueous layer was extracted with EtOAc (2×80 ml). The combined organic phases were evaporated and the residue was purified by Biotage SNAP-Si (100 g) cartridge eluting with a mixture cHex/EtOAc from 80/20 to 50/50. Collected fractions after solvent evaporation afforded the title compound (D8) (5.5 g)

Workup

  1. stirringAfter 30 minutes stirring
  2. stirringThe reaction mixture was stirred at RT for a weekend
  3. customthe phases were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×80 ml)
  5. customThe combined organic phases were evaporated
  6. customthe residue was purified by Biotage SNAP-Si (100 g) cartridge
  7. washeluting with a mixture cHex/EtOAc from 80/20 to 50/50
  8. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-5eb26b201a0740e683555d4ce8c2a7e5
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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