HCID 21193346, compound → HCID 131721222, compound

HRID 443243Notes

Reaction equation

HRID 443243 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24][OH:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(Cl)Cl.CS(C)=O.CCN(CC)CC.[Cl-].[Na+].O>[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH:23]([NH:26][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH:24]=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 1

HCID 21193346HCID 21193346, compound

Product 1

HCID 131721222HCID 131721222, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the alcohol from Step B (135 mg, 0.29 mmol) in CH2Cl2, (1.0 ml), DMSO, (1.0 ml) and Et3N (0.2 ml) at room temperature under argon was added pyridine-SO3 complex (185 mg, 1.17 mmol). The mixture was stirred for 3 hrs and then poured into brine, and extracted with EtOAc. The organic extracts were combined, washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as an oil.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e0b59b82d6e42e39a88e35cb9754450
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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