P-Toluenesulfonamide → HCID 18373353, compound

HRID 2301660Notes

Reaction equation

HRID 2301660 reaction equation
[CH2:1]([C:8]1[CH:45]=[CH:44][C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:20]=3)[C:15]([C:30](=[O:43])[C:31]([NH:33][C:34]3[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=3)[C:37](O)=[O:38])=[O:32])=[CH:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.CCN=C=NCCCN(C)C.[CH3:62][C:63]1[CH:64]=[CH:65][C:66]([S:69]([NH2:72])(=[O:71])=[O:70])=[CH:67][CH:68]=1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:20]=3)[C:15]([C:30](=[O:43])[C:31]([NH:33][C:34]3[CH:42]=[CH:41][CH:40]=[C:36]([C:37]([NH:72][S:69]([C:66]4[CH:65]=[CH:64][C:63]([CH3:62])=[CH:68][CH:67]=4)(=[O:71])=[O:70])=[O:38])[CH:35]=3)=[O:32])=[CH:14]2)=[CH:44][CH:45]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6269P-ToluenesulfonamideHCID 8028TetrahydrofuranHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 18373362HCID 18373362, compound

Product 1

HCID 18373353HCID 18373353, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To the acid obtained in Example 71 (0.1 g) in CH2C2 (10 mL) is added THF (5 mL) to help dissolve the compound. EDCI (0.045 g) and DMAP (0.02 g) was added and the mixture was stirred a room temperature of 1 h. p-Toluenesulfonamide (0.04 g) was added and the reaction was stirred overnight. The reaction mixture was take up in ethyl acetate and washed with water, dried (MgSO4), filtered and concentrated. Chromatography (7% MeOH/CH2Cl2) afforded the title compound (0.045 g, 40%) as a yellow solid. MS: m/z (M-1) 746

Workup

  1. dissolutionto help dissolve the compound
  2. additionwas added
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8317abe114e40aa9dba7746f85374aa
Source dataset
uspto-grants-2002_12
Patent number
US06500853B1

Reaction notes

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