Acetic Acid → HCID 59645174, compound

HRID 2252706Notes

Reaction equation

HRID 2252706 reaction equation
COC1C=CC([N:9](C(C2C=CC=CC=2)C2C=CC=CC=2)[C:10]2[C:11]3[CH:18]=[CH:17][N:16]([C@@H:19]4[O:34][C@H:33]([CH2:35][O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C@@H:22]([O:23][C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C@@:20]4([CH3:44])[OH:21])[C:12]=3[N:13]=[CH:14][N:15]=2)=CC=1.CO.C(O)(=O)C>O>[NH2:9][C:10]1[C:11]2[CH:18]=[CH:17][N:16]([C@@H:19]3[O:34][C@H:33]([CH2:35][O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:38])[CH3:39])[C@@H:22]([O:23][C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C@@:20]3([CH3:44])[OH:21])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 86599742HCID 86599742, compound

Product 1

HCID 59645174HCID 59645174, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the compound from Step I (250 mg, 0.31 mmol) in 6:3:1 MeOH:acetic acid:H2O (10 mL) was stirred at 50° C. for 12 h. The reaction mixture was then concentrated to dryness. The residue was diluted with ethyl acetate (30 mL) and washed with saturated aqueous sodium bicarbonate solution (3×15 mL) and water (2×10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated. The crude product (200 mg) was used without further purification in Step K below. Further purification of a small amount was accomplished by silica gel column chromatography using 5% MeOH in CH2Cl2 as the eluent to give the title compound as a white foam.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. additionThe residue was diluted with ethyl acetate (30 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (3×15 mL) and water (2×10 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product (200 mg) was used without further purification in Step K below
  8. customFurther purification of a small amount

Sources & evidence

ORD record
ord-e5c5318fa4314a6ca7398cd39300abda
Source dataset
uspto-grants-2008_01
Patent number
US07323453B2

Reaction notes

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