Acetic Anhydride → HCID 23648726, compound

HRID 404909Notes

Reaction equation

HRID 404909 reaction equation
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[N:19]=[C:18]([CH:20]([NH2:22])[CH3:21])[O:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>O1CCCC1>[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[N:19]=[C:18]([CH:20]([NH:22][C:34](=[O:36])[CH3:35])[CH3:21])[O:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 23648838HCID 23648838, compound

Product 1

HCID 23648726HCID 23648726, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 40D (265 mg, 0.76 mmol) in tetrahydrofuran (5 mL) at room temperature, was added diisopropylethyl amine (400 uL) followed by acetic anhydride (150 μL, 1.59 mmol). After an hour the reaction was quenched with methanol and stirred for additional hour. The solvent was removed under vacuum and the product was purified via silica-gel column chromatography using a gradient of 25 to 75% ethyl acetate in hexane to provide the title compound (152 mg). 1H NMR (300 MHz, CDCl3) δ ppm 7.90 (s, 1H) 7.17-7.25 (m, 2H) 6.89-6.99 (m, 2H) 6.09 (d, J=7.72 Hz, 1H) 5.33-5.53 (m, 1H) 4.54 (heptet, J=6.0 Hz, 1H) 2.08 (s, 3H) 1.62 (d, J=7.0 Hz, 3H) 1.36 (d, J=6.0 Hz, 6.0H).). MS (DCI): m/z 389 (M+H).

Workup

  1. customAfter an hour the reaction was quenched with methanol
  2. customThe solvent was removed under vacuum
  3. customthe product was purified via silica-gel column chromatography

Sources & evidence

ORD record
ord-a82877a1fa024090aaf06ecc9fe766be
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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