Diethyl Ether → HCID 101928054, compound

HRID 2412670Notes

Reaction equation

HRID 2412670 reaction equation
[CH3:1][CH2:2][C@@H:3]([C@H:5]1[NH:37][C:35](=[O:36])[C@@H:34]([NH:38][C:39]([C@H:41]([N:46]([C:48]([C@H:50]2[N:54]([C:55]([CH:57]([OH:59])[CH3:58])=[O:56])[CH2:53][CH2:52][CH2:51]2)=[O:49])[CH3:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:40])[C@@H:33]([CH3:60])[O:32][C:30](=[O:31])[C@H:29]([CH2:61][C:62]2[CH:63]=[CH:64][C:65]([O:68][CH3:69])=[CH:66][CH:67]=2)[N:28]([CH3:70])[C:26](=[O:27])[C@H:25]2[N:21]([CH2:22][CH2:23][CH2:24]2)[C:19](=[O:20])[C@H:18]([CH2:71][CH:72]([CH3:74])[CH3:73])[NH:17][C:15](=[O:16])[C@@H:14]([CH3:75])[C:12](=[O:13])[C@H:11]([CH:76]([CH3:78])[CH3:77])[O:10][C:8](=[O:9])[CH2:7][C@@H:6]1[OH:79])[CH3:4].[C:80](OC(=O)C)(=[O:82])[CH3:81].[CH3:87][CH2:88][O:89]CC>N1C=CC=CC=1>[CH3:1][CH2:2][CH:3]([C@@H:5]1[NH:37][C:35](=[O:36])[C@@H:34]([NH:38][C:39]([C@@H:41]([N:46]([C:48]([C@H:50]2[N:54]([C:55]([CH:57]([O:59][C:80]([CH3:81])=[O:82])[CH3:58])=[O:56])[CH2:53][CH2:52][CH2:51]2)=[O:49])[CH3:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:40])[C@H:33]([CH3:60])[O:32][C:30](=[O:31])[CH:29]([CH2:61][C:62]2[CH:67]=[CH:66][C:65]([O:68][CH3:69])=[CH:64][CH:63]=2)[N:28]([CH3:70])[C:26](=[O:27])[C@H:25]2[N:21]([CH2:22][CH2:23][CH2:24]2)[C:19](=[O:20])[C@@H:18]([CH2:71][CH:72]([CH3:74])[CH3:73])[NH:17][C:15](=[O:16])[C@@H:14]([CH3:75])[C:12](=[O:13])[C@H:11]([CH:76]([CH3:78])[CH3:77])[O:10][C:8](=[O:9])[CH2:7][C@@H:6]1[O:79][C:88]([CH3:87])=[O:89])[CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 13895197HCID 13895197, compound

Product 1

HCID 101928054HCID 101928054, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A sample of didemnin B (1.0 mg) was dissolved in 1 ml of pyridine and 0.5 ml of acetic anhydride was added. The solution was stirred at room temperature for 18 hours and evaporated to dryness. The residue obtained was dissolved in 3 ml of ether and extracted with water (4×1.5 ml). Evaporation of the dried (Na2SO4) organic phase afforded 0.90 mg (84% yield) of diacetyldidemnin B as a white, amorphous solid, mp 128°-131° C.; Rf 0.65; HPLC retention time (84:16 methanol:water) 9.1 min; EIMS (70 eV) major ions at m/z 70 (100% of base peak), 86 (12), 100 (13), 121 (45), 154 (18), 184 (15), 212 (20), 224 (4), 268 (9), 339 (9), 422 (3); HREIMS gave a molecular ion at m/z 1195.6604 which corresponds to the expected molecular formula C61H93N7O17 (Δ=-2.2 mmu).

Workup

  1. customevaporated to dryness
  2. customThe residue obtained
  3. extractionextracted with water (4×1.5 ml)
  4. customEvaporation of the
  5. dry with materialdried (Na2SO4) organic phase

Sources & evidence

ORD record
ord-579af0cf0d364a8b8c723fd2efd69f5a
Source dataset
uspto-grants-1985_01
Patent number
US04493796

Reaction notes

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