Acetic Anhydride → HCID 86691820, compound

HRID 1059489Notes

Reaction equation

HRID 1059489 reaction equation
[CH3:1][CH2:2][C@@H:3]1[NH:46][C:44](=[O:45])[C@H:43]([C@H:47]([OH:54])[C@@H:48]([CH2:50]/[CH:51]=[CH:52]/[CH3:53])[CH3:49])[N:42]([CH3:55])[C:40](=[O:41])[C@H:39]([CH:56]([CH3:58])[CH3:57])[N:38]([CH3:59])[C:36](=[O:37])[C@H:35]([CH2:60][CH:61]([CH3:63])[CH3:62])[N:34]([CH3:64])[C:32](=[O:33])[C@H:31]([CH2:65][CH:66]([CH3:68])[CH3:67])[N:30]([CH3:69])[C:28](=[O:29])[C@@H:27]([CH3:70])[NH:26][C:24](=[O:25])[C@H:23]([CH3:71])[NH:22][C:20](=[O:21])[C@H:19]([CH2:72][CH:73]([CH3:75])[CH3:74])[N:18]([CH3:76])[C:16](=[O:17])[C@H:15]([CH:77]([CH3:79])[CH3:78])[NH:14][C:12](=[O:13])[C@H:11]([CH2:80][CH:81]([CH3:83])[CH3:82])[N:10]([CH3:84])[C:8](=[O:9])[CH2:7][N:6]([CH3:85])[C:4]1=[O:5].[C:86]([O:89]C(=O)C)(=[O:88])[CH3:87].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>O1CCCC1>[CH3:1][CH2:2][C@@H:3]1[NH:46][C:44](=[O:45])[C@H:43]([C@H:47]([OH:54])[C@@H:48]([CH2:50]/[CH:51]=[CH:52]/[CH3:53])[CH3:49])[N:42]([CH3:55])[C:40](=[O:41])[C@H:39]([CH:56]([CH3:57])[CH3:58])[N:38]([CH3:59])[C:36](=[O:37])[C@H:35]([CH2:60][CH:61]([CH3:62])[CH3:63])[N:34]([CH3:64])[C:32](=[O:33])[C@H:31]([CH2:65][CH:66]([CH3:68])[CH3:67])[N:30]([CH3:69])[C:28](=[O:29])[C@@H:27]([CH3:70])[NH:26][C:24](=[O:25])[C@H:23]([CH3:71])[NH:22][C:20](=[O:21])[C@H:19]([CH2:72][CH:73]([CH3:75])[CH3:74])[N:18]([CH3:76])[C:16](=[O:17])[C@H:15]([CH:77]([CH3:79])[CH3:78])[NH:14][C:12](=[O:13])[C@H:11]([CH2:80][CH:81]([CH3:83])[CH3:82])[N:10]([CH3:84])[C:8](=[O:9])[CH2:7][N:6]([CH3:85])[C:4]1=[O:5].[C:86]([O-:89])(=[O:88])[CH3:87]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 5284373Cyclosporin A

Product 1

HCID 86691820HCID 86691820, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3.6 g (30 mmol) of cyclosporin A in 100 ml tetrahydrofuran were added 1.5 equivalents of acetic anhydride, 1.5 equivalents of triethylamine, and 0.3 g of dimethylaminopyridine. The mixture was refluxed for 18 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate, washed sequentially with 1N hydrochloric acid solution, water, dried over MgSO4 and evaporated. The crude product was chromatographed to give a title compound of 3.2 g.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed sequentially with 1N hydrochloric acid solution, water
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-809e09111fcb4d74b812469a609911b5
Source dataset
uspto-grants-2003_02
Patent number
US06521595B1

Reaction notes

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