Acetic Anhydride → HCID 68873892, compound

HRID 494648Notes

Reaction equation

HRID 494648 reaction equation
[CH3:1][O:2][C:3]1[C@:4]([C:18]([N:20]2[CH2:24][CH2:23][CH2:22][C@@H:21]2[CH2:25][OH:26])=[O:19])([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1.ClCCl>[C:27]([O:26][CH2:25][C@H:21]1[CH2:22][CH2:23][CH2:24][N:20]1[C:18]([C@@:4]1([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:11][CH:12]=[C:3]1[O:2][CH3:1])=[O:19])(=[O:29])[CH3:28]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 68874183HCID 68874183, compound

Product 1

HCID 68873892HCID 68873892, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 171B (54 mg, 0.15 mmol) in anhydrous pyridine (0.5 mL) was added acetic anhydride (50 μL, 0.53 mmol). The resulting mixture was stirred under a N2 atmosphere at r.t. for 16 h, diluted with dichloromethane (10 mL), and extracted with 0.2 N HCl (2× 10 mL). The organic layer was dried over Na2SO4, and the crude product was purified by column chromatography on silica gel using a solvent gradient of 25-50% ethyl acetate in hexane. The title compound was obtained as a colorless solid (50 mg, 83%). 1H NMR (300 MHz, CDCl3) δ 0.51 (m, 1H), 0.71 (d, J=6.62 Hz, 3H), 0.77 (d, J=6.62 Hz, 3H), 0.94 (m, 2H), 1.39 (m, 2H), 1-64 (m, 3H), 2.04 (m, 1H), 2.04 (s, 3H), 2.26 (m, 1H), 2.49 (m, 1H), 3.16 (m, 1H), 3.47 (m, 1H), 3.59 (s, 3H), 4.11 (m, 1H), 4.25 (m, 1H), 4.41 (m, 1H), 4.97 (m, 1H), 7.14 (m, 4H).

Workup

  1. extractionextracted with 0.2 N HCl (2× 10 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe crude product was purified by column chromatography on silica gel using a solvent gradient of 25-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-483540646fdb435e93dbb2fe2a89c601
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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