p-Toluenesulfonic acid → HCID 131725710, compound

HRID 1796873Notes

Reaction equation

HRID 1796873 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:16][CH2:17][S:18][CH2:19][CH3:20])[CH:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1C=CC(S(O)(=O)=O)=C[CH:23]=1>COC(OC)(C)C.C(OCC)(=O)C>[CH2:19]([S:18][CH2:17][CH2:16][C@@H:9]1[CH:10]([C:11]([O:13][CH3:14])=[O:12])[O:15][C:22]([CH3:23])([CH3:21])[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:20]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 91266375HCID 91266375, compound

Product 1

HCID 131725710HCID 131725710, compound

Reagents, catalysts & solvents 2

HCID 64952,2-DimethoxypropaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 21A (1.12 g, 3.65 mmol) and catalytic 4-methylbenzenesulfonic acid (15 mg) in 2,2-dimethoxypropane (35 mL) at ambient temperature was stirred for 36 hours, diluted with ethyl acetate, washed sequentially with aqueous NaHCO3 and pH 7 buffer, dried (MgSO4), filtered, and concentrated. Flash column chromatography (silica gel, 10% acetone/hexanes) provided the desired product. MS (ESI) m/e 348 (M+H)+.

Workup

  1. washwashed sequentially with aqueous NaHCO3 and pH 7 buffer
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ce4fb11699604ceea70ac8d04f23c1f7
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

Loading…