2,5-Dioxopyrrolidin-1-yl (4-bromophenoxy)acetate → 2-(4-Bromophenoxy)-N-[(R)-2-(4-hydroxy-3-methanesulfonylaminophenyl)-2-triethylsilyloxyethyl]acetamide

HRID 2220654Notes

Reaction equation

HRID 2220654 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:12]1[CH:13]=[CH:14][C:15]([OH:23])=[C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:17]=1)[O:4][Si:5]([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:6][CH3:7].[Br:24][C:25]1[CH:42]=[CH:41][C:28]([O:29][CH2:30][C:31](ON2C(=O)CCC2=O)=[O:32])=[CH:27][CH:26]=1>O1CCCC1>[Br:24][C:25]1[CH:42]=[CH:41][C:28]([O:29][CH2:30][C:31]([NH:1][CH2:2][C@@H:3]([C:12]2[CH:13]=[CH:14][C:15]([OH:23])=[C:16]([NH:18][S:19]([CH3:22])(=[O:20])=[O:21])[CH:17]=2)[O:4][Si:5]([CH2:6][CH3:7])([CH2:10][CH3:11])[CH2:8][CH3:9])=[O:32])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 191651892,5-Dioxopyrrolidin-1-yl (4-bromophenoxy)acetateHCID 69202453N-[5-((R)-2-amino-1-triethylsilyloxyethyl)-2-hydroxyphenyl]methanesulfonamide

Product 1

HCID 692001532-(4-Bromophenoxy)-N-[(R)-2-(4-hydroxy-3-methanesulfonylaminophenyl)-2-triethylsilyloxyethyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of N-[5-((R)-2-azido-1-triethylsilyloxyethyl)-2-benzyloxyphenyl]methanesulfonamide (1.84 g) and 10% palladium-carbon (0.18 g) in methanol (15 mL) /methylene chloride (15 mL) was stirred at room temperature for 5 hrs under an atmosphere of hydrogen. The catalyst was removed by filtration, and the solvent was evaporated under reduced pressure to afford N-[5-((R)-2-amino-1-triethylsilyloxyethyl)-2-hydroxyphenyl]methanesulfonamide as a crude product. The crude N-[5-((R)-2-amino-1-triethylsilyloxyethyl)-2-hydroxyphenyl]methanesulfonamide was dissolved in tetrahydrofuran (40 mL), and 2,5-dioxopyrrolidin-1-yl (4-bromophenoxy)acetate (1.39 g) was added to the solution. After being stirred at room temperature for 3 hrs, the reaction mixture was concentrated in vacuo, and the residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to afford the title compound (1.01 g).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a020d01cf819480aae3ac0b0942e44c0
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

Loading…