Octanoyl chloride → HCID 86599742, compound

HRID 2252705Notes

Reaction equation

HRID 2252705 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:10]2[C:11]3[CH:18]=[CH:17][N:16]([C@@H:19]4[O:25][C@H:24]([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C@@H:22]([OH:23])[C@@:20]4([CH3:35])[OH:21])[C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:56](Cl)(=[O:64])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:10]2[C:11]3[CH:18]=[CH:17][N:16]([C@@H:19]4[O:25][C@H:24]([CH2:26][O:27][Si:28]([C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:30])[CH3:29])[C@@H:22]([O:23][C:56](=[O:64])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[C@@:20]4([CH3:35])[OH:21])[C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 86599741HCID 86599741, compound

Product 1

HCID 86599742HCID 86599742, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the compound from Step H (400 mg, 0.6 mmol) and anhydrous DMAP (73 mg, 0.6 mmol) in anhydrous CH2Cl2 (7 mL) was added slowly triethylamine (250 μL, 1.8 mmol). To the stirred solution was added octanoyl chloride (200 μL, 1.2 mmol) over 15 min. The reaction mixture was stirred for an additional 1.5 h. It was then diluted with methylene chloride (30 mL) and washed with saturated aqueous sodium bicarbonate solution (3×10 mL) and water (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated. The residue was subjected to column chromatography on silica gel eluting with 5% MeOH in CH2Cl2 to afford the title compound as a light yellow foam (340 mg).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (3×10 mL) and water (10 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-671cc9f0a65d4dc98085a4827dc1c0a7
Source dataset
uspto-grants-2008_01
Patent number
US07323453B2

Reaction notes

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