4-Toluenesulfonyl chloride → HCID 59161738, compound

HRID 409403Notes

Reaction equation

HRID 409403 reaction equation
[OH:1][CH2:2][CH:3]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.CCN(CC)CC.[S:24](Cl)([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25].[NH4+].[Cl-]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:31][C:30]1[CH:32]=[CH:33][C:27]([S:24]([O:1][CH2:2][CH:3]([NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])[C:4]2[CH:8]=[CH:7][S:6][CH:5]=2)(=[O:26])=[O:25])=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 59161747HCID 59161747, compound

Product 1

HCID 59161738HCID 59161738, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 2-hydroxy-1-(thiophen-3-yl)ethylcarbamate (E1) in CH2Cl2 was added NEt3, DMAP, and TsCl. The solution was stirred at room temperature for 3 hours and then poured into NH4Cl (sat) and extracted with EtOAc, dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 30% EtOAc/Hexanes) gave pure 2-(tert-butoxycarbonylamino)-2-(thiophen-3-yl)ethyl 4-methylbenzenesulfonate (E2).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-680a639c5ead428595b53163a75457fe
Source dataset
uspto-grants-2014_06
Patent number
US08759388B2

Reaction notes

Loading…