Lamellarin T → HCID 16096754, compound

HRID 1060258Notes

Reaction equation

HRID 1060258 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 chromatography 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) δ7.31 (dd, J=2.1, 8.4 Hz, 1H), 7.22 (d, J=2.1 Hz, 1H), 7.14 (d, J=8.7 Hz, 11H), 7.07 (s, 11), 4.90 (m, 1H), 4.60 (m, 1H), 3.90 (s, 3H), 3.89 (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) δ168.7 (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 C34H3, NO11 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-2d7ca91a20ec442e82fdd101a9f5ef26
Source dataset
uspto-grants-2003_02
Patent number
US06521757B1

Reaction notes

Loading…