Acetic Anhydride → HCID 86691820, compound

HRID 1505820Notes

Reaction equation

HRID 1505820 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]>N1C=CC=CC=1.C(OCC)(=O)C>[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

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 5284373Cyclosporin A

Product 1

HCID 86691820HCID 86691820, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 12 g (10 mmol) of Cyclosporin A (MW: 1202.61) in 40 ml of acetic anhydride (MW: 102.09, d 1.082), 40 ml of pyridine (MW: 79.01, d 0.978) and 0.4 g of 4-N,N-dimethylaminopyridine (MW: 122.17) was added. This solution was stirred for overnight at room temperature, and then the mixture was diluted with 600 ml of ethyl acetate. The mixture was washed with brine, saturated ammonium chloride water solution and with 15% of sodium bicarbonate. The organic phase was dried with sodium sulphate. filtered and evaporated under the reduced pressure. The toluene was added to the mixture until all of pyridine was evaporated to yield the pale yellow solid residue, which was purified by flash chromatography on a silica gel column (100-200 mesh) with eluent of ethyl acetate in haxene (1/3) to give the 11.8 g (9.48 mmol, 95%) of Cyclosporin A-acetate (MW: 1244.65).

Workup

  1. washThe mixture was washed with brine, saturated ammonium chloride water solution and with 15% of sodium bicarbonate
  2. dry with materialThe organic phase was dried with sodium sulphate
  3. filtrationfiltered
  4. customevaporated under the reduced pressure
  5. additionThe toluene was added to the mixture until all of pyridine
  6. customwas evaporated
  7. customto yield the pale yellow solid residue, which
  8. customwas purified by flash chromatography on a silica gel column (100-200 mesh) with eluent of ethyl acetate in haxene (1/3)

Sources & evidence

ORD record
ord-db31b0bdbd65484493174d972793ab96
Source dataset
uspto-grants-2015_12
Patent number
US09217015B2

Reaction notes

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