Triethylamine → HCID 131730101, compound

HRID 2191389Notes

Reaction equation

HRID 2191389 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][N:21]([CH2:42][CH:43]([OH:65])[CH2:44][O:45][C:46]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH2:22][CH2:23][O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[C:73](Cl)(=[O:87])[CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:1]([O:18][CH2:19][CH2:20][N:21]([CH2:42][CH:43]([O:65][C:73](=[O:87])[CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86])[CH2:44][O:45][C:46]([C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1)([C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[CH2:22][CH2:23][O:24][Si:25]([C:38]([CH3:39])([CH3:40])[CH3:41])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66986Myristoyl chlorideHCID 69826455HCID 69826455, compound

Product 1

HCID 131730101HCID 131730101, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Another batch of IX was prepared as follows: to a solution of VIII (1.60 g, 1.78 mmol), Et3N (0.50 mL, 3.56 mmol) and DMAP (22 mg, 0.178 mmol), in CH2Cl2 (12 mL) was added dropwise myristoyl chloride (0.53 mL, 1.96 mmol) at 0° C. The reaction mixture was allowed to warm up slowly to room temperature. After stirring 24 h at room temperature, the reaction mixture was diluted with CH2Cl2 (50 mL), washed sequentially with 5% aqueous sodium bicarbonate (15 mL), water (15 mL), and saturated aqueous NaCl (15 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, elution with 0.2% MeOH in CHCl3) furnished 17 (1.60 g, 81%) as oily liquid. NMR spectra coordinates are as follows: 1H NMR (CDCl3): δ 7.34-7.05 (m, 35H), 5.05-4.96 (m, 1H), 3.53-3.42 (m, 4H), 3.08 (dd, J=10.0, 3.2 Hz, 1H), 2.99 (dd, J=10.0, 6.0 Hz, 1H), 2.68-2.54 (m, 6H), 2.25 (t, J=8.0 Hz, 2H), 1.64-1.55 (m, 2H), 1.35-1.14 (m, 20H), 0.98 (s, 118H), 0.88 (t, J=6.8 Hz, 3H).

Workup

  1. washwashed sequentially with 5% aqueous sodium bicarbonate (15 mL), water (15 mL), and saturated aqueous NaCl (15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. washby column chromatography (SiO2, elution with 0.2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-0a9edd2c082c424ba7a154fa363b75db
Source dataset
uspto-grants-2012_12
Patent number
US08329681B2

Reaction notes

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