Toluene-p-sulphonic anhydride → HCID 57540207, compound

HRID 1011465Notes

Reaction equation

HRID 1011465 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([CH2:9][NH:10][C:11](=[O:21])[CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[C:14]2[N+:18]([O-:20])=[O:19])[N:6]=[N:5]1.[O:22](S(C1C=CC(C)=CC=1)(=O)=O)[S:23]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=O)=[O:24]>C(Cl)Cl>[CH3:30][C:29]1[CH:31]=[CH:32][C:26]([S:23]([O:1][CH2:2][CH2:3][N:4]2[CH:8]=[C:7]([CH2:9][NH:10][C:11](=[O:21])[CH2:12][N:13]3[CH:17]=[CH:16][N:15]=[C:14]3[N+:18]([O-:20])=[O:19])[N:6]=[N:5]2)(=[O:24])=[O:22])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 77773Toluene-p-sulphonic anhydrideHCID 57540206HCID 57540206, compound

Product 1

HCID 57540207HCID 57540207, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added the alcohol 20 (106 mg, 0.359 mmol), TEA (36.3 mg, 0.359 mmol) and DCM (10 mL). Ts2O (117 mg, 0.359 mmol) was added in one portion. The reaction was stirred at RT for 4 hrs. The reaction was then concentrated to dryness and purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 55 mg (34% yield) of 21 as a white solid. Mass Spec (lo-res): Calc'd for C17H19N7O6S: 449.11; found: 450.1 (M+H).

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. custompurified on a silica gel cartridge

Sources & evidence

ORD record
ord-e3c82f16791e4feebadaa1d028f9ddc2
Source dataset
uspto-grants-2011_07
Patent number
US07977361B2

Reaction notes

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