Octanoyl chloride → HCID 71549357, compound

HRID 1852359Notes

Reaction equation

HRID 1852359 reaction equation
[NH2:1][C@H:2]([CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C@@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[OH:4].CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>C1COCC1.CCOC(C)=O>[OH:4][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[C@H:2]([NH:1][C:28](=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 8124Octanoyl chlorideHCID 81531DiisopropylethylamineHCID 86680953HCID 86680953, compound2×

Product 1

HCID 71549357HCID 71549357, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of (1R,2R)-2-amino-1-(2-methoxyphenyl)-3-(pyrrolidin-1-yl)propan-1-ol (0.1 g, 0.40 mmol) (compound 6) in THF (5 ml) was added Hunig's Base (0.07 g, 0.52 mmol), followed by the dropwise addition of octanoyl chloride (0.07 g, 0.40 mmol). 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. Purified by flash silica chromatography (MeOH/CH2Cl2) to give a yellow oil (0.03 g, 0.09 mmol, 22% yield). HPLC purity 93% (tR=5.3 min) NMR (500 MHz, CDCl3) δ 7.4 (m, 1H), 7.2-7.3 (m, 1H), 6.9-7.0 (m, 1H), 6.8-6.9 (m, 1H), 6.0-6.1 (m, 1H), 5.3 (d, 1H), 4.2-4.3 (m, 1H), 3.8 (s, 3H), 2.9-3.0 (m, 3H), 2.5-2.7 (m, 4H), 2.0-2.1 (m, 2H), 1.7-1.8 (m, 4H), 1.9-2.0 (m, 2H), 1.2-1.4 (m, 6H), 0.8-0.9 (t, 3H). ESI-MS m/z 377.2 (M+H +).

Workup

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

Sources & evidence

ORD record
ord-c6d1b963e306440e9f2c84bd315e06e8
Source dataset
uspto-grants-2015_02
Patent number
US08961959B2

Reaction notes

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