Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 123640282, compound

HRID 711201Notes

Reaction equation

HRID 711201 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C@@H:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:17]([O:24][C:25]3[CH:26]=[CH:27][C:28]4[N:29]([C:31]([N:34]5[CH2:39][CH2:38][CH2:37][CH2:36][C@@H:35]5[CH3:40])=[N:32][N:33]=4)[CH:30]=3)[CH2:16][CH2:15]2)=[O:12])[N:7]([C:41]2[C:42]([CH2:55][O:56][Si:57]([CH:64]([CH3:66])[CH3:65])([CH:61]([CH3:63])[CH3:62])[CH:58]([CH3:60])[CH3:59])=[N:43][N:44]([CH2:46][CH2:47][O:48]C3CCCCO3)[CH:45]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C@@H:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:17]([O:24][C:25]3[CH:26]=[CH:27][C:28]4[N:29]([C:31]([N:34]5[CH2:39][CH2:38][CH2:37][CH2:36][C@@H:35]5[CH3:40])=[N:32][N:33]=4)[CH:30]=3)[CH2:16][CH2:15]2)=[O:12])[N:7]([C:41]2[C:42]([CH2:55][O:56][Si:57]([CH:61]([CH3:63])[CH3:62])([CH:64]([CH3:66])[CH3:65])[CH:58]([CH3:59])[CH3:60])=[N:43][N:44]([CH2:46][CH2:47][OH:48])[CH:45]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 123384314HCID 123384314, compound

Product 1

HCID 123640282HCID 123640282, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of Intermediate 74h (0.34 g, 0.37 mmol) in MeOH (3.7 mL) was treated with pyridinium p-toluenesulfonate (0.28 g, 1.1 mmol) and the mixture was stirred at 45° C. for 24 h. The mixture was evaporated in vacuo and the residue was partitioned between DCM and a saturated aqueous sodium bicarbonate solution. The aqueous layer was then extracted with DCM (2×). The combined organic layers were washed with water, a saturated aqueous sodium bicarbonate solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-8% MeOH in DCM, to give the title compound as a golden glass (142 mg, 46%). LCMS (Method 3): Rt 4.81 min, m/z 839.6 [MH+].

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was partitioned between DCM
  3. extractionThe aqueous layer was then extracted with DCM (2×)
  4. washThe combined organic layers were washed with water
  5. dry with materiala saturated aqueous sodium bicarbonate solution and brine, dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-b1ca3a2add694a57abd8c4514da85811
Source dataset
uspto-grants-2015_11
Patent number
US09181242B2

Reaction notes

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