Benzenepropanoyl chloride → HCID 71549356, compound

HRID 1852357Notes

Reaction equation

HRID 1852357 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C@@H:11]([OH:21])[C@H:12]([NH:19][CH3:20])[CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:9]=[CH:10][C:2]1=2.CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:40])[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1.CCOC(C)=O>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C@@H:11]([OH:21])[C@H:12]([N:19]([CH3:20])[C:31](=[O:40])[CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:13][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 3

HCID 64801Benzenepropanoyl chlorideHCID 81531DiisopropylethylamineHCID 86680951HCID 86680951, compound

Product 1

HCID 71549356HCID 71549356, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of compound 5 (0.2 g, 0.72 mmol) in THF (4 mL) was added Hunig's Base (0.09 g, 0.72 mmol) followed by hydrocinnamoyl chloride (0.12 g, 0.72 mmol) dropwise. The resulting mixture was allowed to stir overnight at room temperature, diluted with EtOAc and washed with satd. aq. NaHCO3, satd. aq. NaCl and dried over MgSO4. Purification by flash silica chromatography (MeOH/CH2Cl2) gave a yellow oil (0.12 g, 0.29 mmol, 41% yield). HPLC purity 98.4% (tR=5.02 min). NMR (500 MHz, CDCl3) δ 7.2 (s, 1H), 7.1-7.2 (m, 4H), 6.8-6.9 (m, 3H), 4.8 (s, 1H), 4.3 (s, 4H), 2.9 (s, 3H), 2.8-3.2 (m, 4H), 2.5-2.6 (m, 2H), 1.8-2.1 (m, 2H), 1.5-1.8 (m, 4H). ESI-MS m/z 425.1 (M+H+).

Workup

  1. washwashed with satd
  2. dry with materialaq. NaCl and dried over MgSO4
  3. customPurification by flash silica chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-984af9feb6e04936bf7eaa5b30961c59
Source dataset
uspto-grants-2015_02
Patent number
US08961959B2

Reaction notes

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