Acetic Anhydride → HCID 22999720, compound

HRID 397285Notes

Reaction equation

HRID 397285 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([O:7][CH2:8][CH2:9][OH:10])[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>O1CCCC1>[C:34]([O:10][CH2:9][CH2:8][O:7][C:4]1[C:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:2]([NH2:1])[O:6][N:5]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 21598884HCID 21598884, compound

Product 1

HCID 22999720HCID 22999720, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of tert-butyl 5-amino-3-(2-hydroxyethoxy)-4-isoxazolecarboxylate (R. Neidlein, J.Heterocyclic Chem., 1989, 26,1335) (5.60 g) and triethylamine (3.36 ml) in tetrahydrofuran (50 ml) at room temperature was added dimethylaminopyridine (280 mg) followed by acetic anhydride (2.81 g). The reaction was stirred for 2 hours at room temperature. The solvent was removed in vacuo to yield the crude material (6.0 g). The crude material was purified using the Biotage™ Flash 40i System (silica, 90 g), eluting with ethyl acetate:hexane (1:1) to yield the product as an off white solid (5.0 g)

Workup

  1. customThe solvent was removed in vacuo
  2. customto yield the crude material (6.0 g)
  3. customThe crude material was purified
  4. washeluting with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record
ord-b0d3ffeac80b4a6ebe1296de29cf3c21
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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