Palmitic Acid → HCID 67436289, compound

HRID 468222Notes

Reaction equation

HRID 468222 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[C:16]([OH:33])(=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[CH2:34]([O:41][CH2:42][C@H:43](O)[CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]/[CH:54]=[CH:55]\[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(Cl)(Cl)Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:34]([O:41][CH2:42][C@H:43]([O:32][C:16](=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]/[CH:54]=[CH:55]\[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 985Palmitic AcidHCID 6212Chloroform2×HCID 10868DicyclohexylcarbodiimideHCID 67436714HCID 67436714, compound

Product 1

HCID 67436289HCID 67436289, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A 4 mL solution of DCC (111 mg, 0.54 mmol), DMAP (3 mg, 0.02 mmol) and palmitic acid (86 mg, 0.34 mmol) in CH2Cl2 was cooled to 0° C. A solution of 3-O-benzyl-1-O-oleyl-sn-glycerol (100 mg, 0.228 mmol) in CH2Cl2 (2 mL) was added to it in a drop-wise manner and stirred for 12 h at rt. The mixture was filtered over Celite, washed with saturated aqueous sodium bicarbonate solution and brine, dried on anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography using silica gel (hexane:EtOAc=15:1, Rf=0.35) to get the product (154 mg, quantitative) as colorless oil. [α]D28+5° (c=2.0, CHCl3); IR (CHCl3) cm−1 2924, 2854, 1742, 1651, 1460, 1369, 1241, 1164, 1109, 1028, 733, 698 cm−1; 1H NMR (600 MHz, CDCl3) δ 0.88 (t, J=7.2 Hz, 6H, CH3), 1.22-1.38 (m, 44H, CH2), 1.52 (dt, J=7.2, 14.4 Hz, 4H, CH2), 1.94 (dd, J=6.6, 12.6 Hz, 4H, CH2), 2.20 (t, J=7.8 Hz, 2H, CH2), 2.24 (t, J=7.8 Hz, 2H, CH2), 3.51 (ddd, J=5.0, 10.2, 15.6 Hz, 2H, CH2OBn), 4.11 (dd, J=5.4, 12.0 Hz, 1H, CH2OAcyl), 4.27 (dd, J=3.6, 12.0 Hz, 1H, CH2OAcyl), 4.44, 4.48 (AB q, J=12.0 Hz, 2H, PhCH2), 4.06 (dt, J=4.2, 9.0 Hz, 1H, CH), 5.35 (ddd, J=6.0, 11.4, 15.6 Hz, 2H, CH═CH 7.20-7.32 (m, 5H, ArH); 13C NMR (150 MHz, CDCl3) δ 14.1, 22.65, 22.66, 24.8, 24.9, 27.1, 27.2, 29.06, 29.09, 29.16, 29.27, 29.29, 29.33, 29.46, 29.50, 29.61, 29.63, 29.67, 29.74, 31.88, 31.90, 34.1, 34.3, 62.6, 68.2, 70.0, 73.3, 127.6, 127.7, 128.4, 129.7, 130.0, 137.7, 173.0, 173.3; EMSI calc'd for C44H76NaO5 [M+Na]+ 707.56. found: 707.50.

Workup

  1. filtrationThe mixture was filtered over Celite
  2. washwashed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography
  6. customto get the product (154 mg, quantitative) as colorless oil

Sources & evidence

ORD record
ord-c4166bb8db5d48e6ad3631b844296851
Source dataset
uspto-grants-2014_01
Patent number
US08624006B2

Reaction notes

Loading…