Acetic Anhydride → Methyl (2r)-{4-[2-(acetylamino)ethoxy]phenyl}({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-ethanoate

HRID 1976444Notes

Reaction equation

HRID 1976444 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1>[C:31]([NH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:16][S:17]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 131722539Methyl(2r)-[4-(2-aminoethoxy)phenyl]({[4(2-butynyloxy)phenyl]sulfonyl}amino)ethanoate

Product 1

HCID 91298855Methyl (2r)-{4-[2-(acetylamino)ethoxy]phenyl}({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-ethanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.219 g (0.507 mmol) of methyl(2R)-[4-(2-aminoethoxy)phenyl]({[4(2-butynyloxy)phenyl]sulfonyl}amino)ethanoate in 2.5 mL of acetic anhydride and 0.25 mL of pyridine was stirred at room temperature for 15 h and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:1) to provide 0.213 g of methyl (2R)-{4-[2-(acetylamino)ethoxy]phenyl}({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-ethanoate as a white foam. Electrospray Mass Spec 475.3 (M+H)+

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-19310ee833174082a267bb201c268f19
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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