Lamellarin T → HCID 16096754, compound

HRID 225520Notes

Reaction equation

HRID 225520 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:21]3[C:22]4[C:27]([O:28][C:29](=[O:30])[C:20]=3[N:19]3[C:10]=2[C:11]2[C:16]([CH2:17][CH2:18]3)=[C:15]([O:34][CH3:35])[C:14]([O:36][CH3:37])=[C:13]([O:38][CH3:39])[CH:12]=2)=[CH:26][C:25]([OH:31])=[C:24]([O:32][CH3:33])[CH:23]=4)=[CH:5][C:4]=1[OH:40]>C(OC(=O)C)(=O)C.N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:4][C:3]([O:40][C:4]1[CH:5]=[C:6]([C:9]2[C:21]3[C:22]4[C:27]([O:28][C:29](=[O:30])[C:20]=3[N:19]3[C:10]=2[C:11]2[C:16]([CH2:17][CH2:18]3)=[C:15]([O:34][CH3:35])[C:14]([O:36][CH3:37])=[C:13]([O:38][CH3:39])[CH:12]=2)=[CH:26][C:25]([O:31][C:27]([CH3:26])=[O:28])=[C:24]([O:32][CH3:33])[CH:23]=4)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:2]

Participants

6

Reactant 1

HCID 5481589Lamellarin T

Product 1

HCID 16096754HCID 16096754, compoundYield 169.7%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
18 °C

Procedure

Lamellarin T (48 mg, 0.088 mmol) was dissolved in a solution of acetic anhydride (1.0 mL) and pyridine (1.0 mL) containing DMAP (several crystals) and the solution stirred at 18° C. for 26 h. The solution was then diluted with ethyl acetate (15 mL) and washed with NaHCO3 (a saturated solution in H2O, 20 mL) and citric acid (10% in H2O, 20 mL) dried over (MgSO4) and concentrated under reduced pressure. The residue was subjected to flash chromatograophy on silica gel (sequential elution with 2:1, 1:1 hexane/ethyl acetate) the relevant fractions (Rf 0.42 1:1 hexane/ethyl acetate) were concentrated giving the title compound (47 mg, 83%) as a white solid mp 251-2° C. IR (KBr disc, cm−1) 2937, 2840, 1769, 1718, 1603, 1545, 1507, 1475, 1456, 1414, 1295, 1266, 1201, 1141, 1117, 1036. 1H NMR (300 MHz, CDCl3) δ 7.31 (dd, J=2.1, 8.4 Hz, 1H), 7.22 (d, J=2.1 Hz, 1H), 7.14 (d, J=8.7 Hz, 1H), 7.07 (s, 1H), 4.90 (m, 1H), 4.60 (m, 1H), 3.90 (s, 3H), 3.89 (s, 3H), 3.86 (s, 3H), 3.45 (s, 3H), 3.39 (s, 3H), 3.13 (m, 2H), 2.30 (s, 6H). 13C NMR+APT (75.5 MHz, CDCl3) δ 168.7 (C), 168.4 (C), 155.0 (C), 151.9 (C), 147.5 (C), 144.8 (C), 142.2 (C), 140.6 (C), 138.7 (C), 135.6 (C), 129.5 (CH), 127.6 (C), 127.2 (C), 125.4 (CH), 122.6 (C), 119.8 (C), 116.1 (C), 114.8 (C), 114.4 (C), 112.9 (CH), 111.7 (CH), 105.4 (CH), 105.0 (CH), 60.9 (CH3), 60.8 (CH3), 56.2 (CH3), 55.5 (CH3), 55.2 (CH3), 42.1 (CH2), 21.7 (CH2), 20.4 (CH3). MS (70 eV) m/z (%): 629 (53, M+·), 587 (100, M+·-CH2CO); HRMS calcd for C34H31NO11 629.1897. Found 629.1907.

Workup

  1. washwashed with NaHCO3 (a saturated solution in H2O
  2. dry with material20 mL) and citric acid (10% in H2O, 20 mL) dried over (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. concentrationwere concentrated

Sources & evidence

ORD record
ord-9443f323c6254afda641fc07de7dce7f
Source dataset
uspto-grants-2009_07
Patent number
US07557118B2

Reaction notes

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