Water TFA acetonitrile → HCID 22954742, compound

HRID 2230474Notes

Reaction equation

HRID 2230474 reaction equation
[C:1]([C:9]([NH:11][CH:12]1[C:18](=[O:19])[N:17]2[CH:20]([C:24]([NH:26][CH:27]3[CH2:31][C:30](=[O:32])[O:29][CH:28]3[O:33]CC3C=CC=CC=3)=[O:25])[CH2:21][CH2:22][CH2:23][N:16]2[C:15](=[O:41])[CH2:14][CH2:13]1)=[O:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.CC#N.O>>[C:1]([C:9]([NH:11][CH:12]1[C:18](=[O:19])[N:17]2[CH:20]([C:24]([NH:26][CH:27]([CH:28]=[O:33])[CH2:31][C:30]([OH:32])=[O:29])=[O:25])[CH2:21][CH2:22][CH2:23][N:16]2[C:15](=[O:41])[CH2:14][CH2:13]1)=[O:10])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 22145617Water TFA acetonitrileHCID 72603756HCID 72603756, compound

Product 1

HCID 22954742HCID 22954742, compoundYield 99.1%

Procedure

Compound 2001 (58.6 mg, 0.10 mmol) was treated with 15 mg of TFA/MeCN/water (1:2:3) and stirred at room temperature for 6.5 h. The reaction was extracted with ether. The aqueous layer was concentrated with azeotropic removal of the water using MeCN. The product was suspended in CH2Cl2, concentrated in vacuo and precipitated with ether to give 46.8 mg (99%) of 2002 as a white solid: 1H NMR (CD3OD) δ9.05 (0.25H, d), 8.15 (1H, d), 7.68 (1H, t), 7.64 (0.25H, d), 7.55 (3H, t), 7.35 (0.5H, m), 5.22 (1H, t), 4.90 (1H, m), 4.58 (1H, dd), 4.50 (1H, m), 4.28 (1H, bm), 3.45 (1H, m), 3.10 (1H, bt), 2.68 (1H, ddd), 2.60-2.45 (2H, m), 2.30 (1H, dd), 2.15-2.05 (2H, m), 1.90 (2H, bm), 1.68 (1H, bm).

Workup

  1. extractionThe reaction was extracted with ether
  2. concentrationThe aqueous layer was concentrated with azeotropic removal of the water
  3. concentrationconcentrated in vacuo
  4. customprecipitated with ether

Sources & evidence

ORD record
ord-7526fffe1a4548d8af40c7aea1f0d79d
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

Loading…