p-Bromobenzenesulfonyl chloride → tert-Butyl 1-(3-(4-bromophenylsulfonamido)phenyl)-2-(tert-butyldimethylsilyloxy)ethyl(2-methoxyethyl)carbamate

HRID 221410Notes

Reaction equation

HRID 221410 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([N:18]([CH2:26][CH2:27][O:28][CH3:29])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[Br:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl.CCOC(C)=O>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]([N:18]([CH2:26][CH2:27][O:28][CH3:29])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13])[CH:5]=[CH:6][CH:7]=2)(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58378837tert-Butyl 1-(3-aminophenyl)-2-(tert-butyldimethylsilyloxy)ethyl(2-methoxyethyl)carbamate

Product 1

HCID 70911548tert-Butyl 1-(3-(4-bromophenylsulfonamido)phenyl)-2-(tert-butyldimethylsilyloxy)ethyl(2-methoxyethyl)carbamateYield 23.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of tert-butyl 1-(3-aminophenyl)-2-(tert-butyldimethylsilyloxy)ethyl(2-methoxyethyl)carbamate (0.5 g, 1.95 mmol) and 4-bromobenzenesulfonyl chloride (0.99 g) in chloroform (20 mL) was stirred under nitrogen at room temperature. N,N-Diisopropyl ethyl amine (1 mL) was added and the mixture was stirred for 16 hours at 60° C. The solution was diluted with EtOAc (50 mL), washed with water (2×20 mL), 1 M HCl (20 mL) and brine (20 mL) and dried over Na2SO4. Evaporation of the solvents gave a brown oil which was purified by column chromatography (30% EtOAc in hexane) to give the title compound as a light yellow oil (0.3 g).

Workup

  1. stirringthe mixture was stirred for 16 hours at 60° C
  2. washwashed with water (2×20 mL), 1 M HCl (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvents
  5. customgave a brown oil which
  6. customwas purified by column chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-2863a6b584eb4a339babdcb8a77f90bc
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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