4-Toluenesulfonyl chloride → HCID 86632370, compound

HRID 2428156Notes

Reaction equation

HRID 2428156 reaction equation
CCN(CC)CC.[C:8]([O:12][C:13](=[O:29])[N:14]([CH2:18][C:19]1[CH:24]=[C:23]([CH2:25][CH2:26][OH:27])[CH:22]=[CH:21][C:20]=1[Cl:28])[CH:15]1[CH2:17][CH2:16]1)([CH3:11])([CH3:10])[CH3:9].[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:8]([O:12][C:13]([N:14]([CH2:18][C:19]1[CH:24]=[C:23]([CH2:25][CH2:26][O:27][S:36]([C:33]2[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=2)(=[O:38])=[O:37])[CH:22]=[CH:21][C:20]=1[Cl:28])[CH:15]1[CH2:16][CH2:17]1)=[O:29])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 67148838HCID 67148838, compound

Product 1

HCID 86632370HCID 86632370, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Et3N (2.56 mL, 18.4 mmol) and DMAP (153 mg, 1.23 mmol) were added to a sol. of [2-chloro-5-(2-hydroxy-ethyl)-benzyl]-cyclopropyl-carbamic acid tert-butyl ester (4.00 g, 12.3 mmol) in CH2Cl2 (110 mL) at 0° C. A sol. of p-toluenesulfonyl chloride (2.80 g, 14.7 mmol) in CH2Cl2 (18 mL) was added dropwise, and the mixture was stirred for 3 days while warming up to rt. The mixture was partitioned between CH2Cl2 and water, and the aq. layer was extracted with CH2Cl2 (3×). The combined org. layers were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (heptane/EtOAc 8:2) yielded the title compound (4.90 g, 83%). LC-MS: tR=1.13 min; ES+: 480.53.

Workup

  1. customThe mixture was partitioned between CH2Cl2 and water
  2. extractionthe aq. layer was extracted with CH2Cl2 (3×)
  3. washlayers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the crude by FC (heptane/EtOAc 8:2)

Sources & evidence

ORD record
ord-c742d25cceb2401f8f334e05acca814d
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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