4-Toluenesulfonyl chloride → HCID 19874920, compound

HRID 465636Notes

Reaction equation

HRID 465636 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:29])[CH2:15][NH:16][CH2:17][C:18]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH3:3].C(N(CC)CC)C.[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1>C(OCC)(=O)C>[CH3:3][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:11])[CH3:12])[C:5]=1[NH:13][C:14](=[O:29])[CH2:15][N:16]([S:43]([C:40]1[CH:41]=[CH:42][C:37]([CH3:47])=[CH:38][CH:39]=1)(=[O:45])=[O:44])[CH2:17][C:18]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH3:1]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 19874901HCID 19874901, compound

Product 1

HCID 19874920HCID 19874920, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the product of Example 6 (0.45 g) and excess triethylamine at room temperature was added 0.22 g p-toluene sulfonyl chloride. This mixture was diluted with ethyl acetate, concentrated, and triethylamine and ethyl acetate added a second time. The reaction mixture was then concentrated to a brown oil. After sitting 5 days at room temperature, the oil was taken up in ethyl acetate, washed with NaHCO3 and NaCl solutions, dried over MgSO4, filtered, and concentrated to an oil. The oil was purified by chromatography on silica gel using hexane/EtoAc, 8/21 as eluant. The appropriate fractions were concentrated to an oil which crystallized upon trituration with hexane. 0.44 g (69%). NMR (CDCl3) δ 1.17 (6H, d), δ 1.64-1.82 (4H, m), δ 2.03 (4H, m), δ 2.42 (3H, s), δ 2.97 (2H, m), δ 3.42 (2H, s), δ 3.55 (2H, s), δ 7.13-7.65 (12H, m). IR (KBr) 3370, 2965, 2870, 1673, 1497, 1328, 1158, 1092, 755, 550 cm-1.

Workup

  1. concentrationconcentrated
  2. additiontriethylamine and ethyl acetate added a second time
  3. concentrationThe reaction mixture was then concentrated to a brown oil
  4. washwashed with NaHCO3 and NaCl solutions
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customThe oil was purified by chromatography on silica gel
  9. concentrationThe appropriate fractions were concentrated to an oil which
  10. customcrystallized upon trituration with hexane

Sources & evidence

ORD record
ord-7c877f05cd0a4eb49dc2a0e09e5409e0
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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