Succinic anhydride → HCID 89998992, compound

HRID 2273334Notes

Reaction equation

HRID 2273334 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH3:8][O:9][C:10]1[CH:44]=[CH:43][C:13]([CH2:14][O:15][C@@H:16]2[C@@H:23]([CH2:24][OH:25])[O:22][C@H:19]([O:20][CH3:21])[C@H:18]([OH:26])[C@H:17]2[O:27][C:28](=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:12][CH:11]=1.[C:45](Cl)(=[O:59])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:4]([CH2:3][CH2:2][C:1]([O:25][CH2:24][C@H:23]1[O:22][C@H:19]([O:20][CH3:21])[C@H:18]([O:26][C:45](=[O:59])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C@@H:17]([O:27][C:28](=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C@@H:16]1[O:15][CH2:14][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:44][CH:43]=1)=[O:7])([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 66986Myristoyl chlorideHCID 89998693HCID 89998693, compound

Product 1

HCID 89998992HCID 89998992, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

DMAP (8.1 mg, 0.06 mmol) and succinic anhydride (67 mg, 0.67 mmol) were added to a stirred solution of derivative 16 (0.35 g, 0.67 mmol) in dry pyridine (5 mL) and the resulting mixture was stirred for 16 h at rt under argon. After that, myristoyl chloride (0.21 ml, 0.80 mmol) was added dropwise, and the reaction mixture was stirred for 2 h at rt. After that, the resulting mixture was concentrated under the reduced pressure. The residue was dissolved in CH2Cl2 (30 mL) and washed successively with 1N HCl (2×15 mL), water (2×15 mL) and brine (15 mL). The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-hexane gradient elution) to give compound 17 (0.43 g, 0.52 mmol) as white syrup in 79% yield. Analytical data for 17: Rf=0.55 (ethyl acetate-hexane 1/1, v/v); [α]D24+42.4° (c=1.0, CHCl3); 1H NMR (300 MHz, CDCl3): δ, 0.87 (t, 6H, 2×CH3), 1.25 (br. s, 40H, 20×CH2), 1.59 (m, 4H, 2×CH2), 2.26 (m, 2H, CH2), 2.33 (m, 2H, CH2), 2.61 (m, 4H, 2×CH2), 3.36 (s, 3H, OCH3), 3.59 (dd, 1H, J4,5=9.5 Hz, H-4), 3.90 (m, 1H, H-5), 4.28 (dd, 2H, J5,6b=4.4 Hz, J6a,6b=11.5 Hz, H-6a, 6b), 4.44 (d, 1H, J2=10.7 Hz, ½CH2Ph), 4.54 (d, 1H, J2=10.7, ½CH2Ph), 4.87 (m, 2H, H-1, 2), 5.55 (dd, 1H, J3,4=9.5 Hz, H-3), 6.84 (d, 2H, J=8.7 Hz, aromatic), 7.16 (d, 2H, J=8.6 Hz, aromatic) ppm; 13C NMR (75 MHz, CDCl3): δ, 14.3, 22.8, 25.1, 28.8, 29.2, 29.3, 29.4 (×2), 29.5, 29.6, 29.7, 29.8, 32.1, 34.2, 34.5 (×3), 55.4, 62.7, 68.6, 71.8, 71.9, 74.3, 75.7, 96.9, 114.0, 129.5, 129.8, 159.6, 171.7, 172.8, 173.7 ppm; HR FAB MS [M+Na]+ calcd for C47H78O12Na 857.5391. found 857.5410.

Workup

  1. stirringthe reaction mixture was stirred for 2 h at rt
  2. concentrationAfter that, the resulting mixture was concentrated under the reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2 (30 mL)
  4. washwashed successively with 1N HCl (2×15 mL), water (2×15 mL) and brine (15 mL)
  5. customThe organic phase was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate-hexane gradient elution)

Sources & evidence

ORD record
ord-ea1ef13dc1e245859ef80a37a1544c04
Source dataset
uspto-grants-2015_09
Patent number
US09120838B2

Reaction notes

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