4-Toluenesulfonyl chloride → HCID 57186074, compound

HRID 722878Notes

Reaction equation

HRID 722878 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][C@@H:8]([CH2:17][OH:18])[CH2:9][C@H:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:19])[CH2:7][C@@H:8]([CH2:17][O:18][S:20]([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:9][C@H:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 57080220HCID 57080220, compound

Product 1

HCID 57186074HCID 57186074, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 158 (2.27 g, 8.33 mmol) was dissolved in CH2Cl2 (30 mL) and cooled to 0° C. Tosyl chloride (1.91 g, 10.0 mmol) and catalytic DMAP were added, followed by dropwise addition of triethylamine (2.55 mL, 18.33 mmol). The reaction was then stirred at 0° C. for 18 hours. The solvent was rotovapped off (removed under reduced pressure), and the crude material washed with EtOAc and filtered. The solids were washed with EtOAc, and the filtrate washed with 0.5N HCl (20 mL), brine (30 mL), dried over MgSO4, filtered, and rotovapped. The oil was chromatographed on silica eluting with a 5% EtOAc/hexanes gradient to 10% EtOAc/hexanes to give 159 (3.399 g, 96%) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.75 (d, J=8.30 Hz, 2H), 7.31 (d, J=8.30 Hz, 2H), 3.99 (dd, J=9.65, 3.54 Hz, 1H), 3.89 (dd, J=9.52, 5.37 Hz, 1H), 2.42 (s, 3H), 2.28 (dd, J=14.7, 6.23 Hz, 1H), 2.19–2.14 (m, 1H), 2.10 (dd, J=14.9, 6.35 Hz, 1H), 1.38 (s, 9H), 1.31–1.17 (m, 3H), 1.08–0.81 (m, 2H), 0.79–0.76 (m, 6H); [α]D=−10.1 (c1 in CHCl3).

Workup

  1. custom(removed under reduced pressure)
  2. washthe crude material washed with EtOAc
  3. filtrationfiltered
  4. washThe solids were washed with EtOAc
  5. washthe filtrate washed with 0.5N HCl (20 mL), brine (30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe oil was chromatographed on silica eluting with a 5% EtOAc/hexanes gradient to 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-6e23d27856184c348451e890a79162d4
Source dataset
uspto-grants-2006_11
Patent number
US07138542B2

Reaction notes

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