Methanol → HCID 22829433, compound

HRID 1955302Notes

Reaction equation

HRID 1955302 reaction equation
[CH3:1][CH2:2][C@@H:3]1[C:76](=[O:77])[NH:75][C@@:6]2([O:11][C@@H:10]([CH2:12][C@H:13]([OH:71])[C@H:14]([CH2:16][CH2:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](/[C@H:23]3[O:51][C:49](=[O:50])[C@H:47]4[NH:48][N:43]([CH2:44][CH2:45][CH2:46]4)[C:41](=[O:42])[C@H:40]([CH2:52][C:53]4[CH:54]=[CH:55][CH:56]=[C:57]([OH:59])[CH:58]=4)[NH:39][C:37](=[O:38])[C@H:36]([CH:60]([CH3:62])[CH3:61])[NH:35][C:33](=[O:34])[C@H:32]([CH2:63][CH2:64][C:65]([CH3:67])=[O:66])[C@H:31]([OH:68])[C@@H:30]([CH3:69])[C@@H:29]([OH:70])[CH:28]=[CH:27][CH:26]=[CH:25][CH2:24]3)\[CH3:22])[CH3:15])[C@H:9]([CH3:72])[C@H:8]([OH:73])[C@@H:7]2[CH3:74])[C@@H:5]([CH3:78])[CH2:4]1.[CH3:79]O>>[CH3:1][CH2:2][C@@H:3]1[C:76](=[O:77])[NH:75][C@@:6]2([O:11][C@@H:10]([CH2:12][C@H:13]([OH:71])[C@H:14]([CH2:16][CH2:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](/[C@H:23]3[O:51][C:49](=[O:50])[C@@H:47]4[NH:48][N:43]([CH2:44][CH2:45][CH2:46]4)[C:41](=[O:42])[C@H:40]([CH2:52][C:53]4[CH:54]=[CH:55][CH:56]=[C:57]([OH:59])[CH:58]=4)[NH:39][C:37](=[O:38])[C@H:36]([CH:60]([CH3:61])[CH3:62])[NH:35][C:33](=[O:34])[C@@H:32]4[CH2:63][CH2:64][C@:65]([O:66][CH3:79])([CH3:67])[O:68][C@@H:31]4[C@@H:30]([CH3:69])[C@@H:29]([OH:70])[CH:28]=[CH:27][CH:26]=[CH:25][CH2:24]3)\[CH3:22])[CH3:15])[C@H:9]([CH3:72])[C@H:8]([OH:73])[C@@H:7]2[CH3:74])[C@@H:5]([CH3:78])[CH2:4]1

Participants

3

Reactant 2

HCID 887MethanolHCID 5388925Sanglifehrin A

Product 1

HCID 22829433HCID 22829433, compound

Procedure

To a stirred, cooled (0° C.) solution of 20 mg (18.3 μmol) of Sanglifehrin A in 0.5 mL of methanol is added one crystal of paratoluenesulfonic acid monohydrate. The resulting yellow solution is stirred for one hour and the reaction is quenched with saturated aqueous sodium bicarbonate solution. The resulting mixture is extracted twice with ethyl acetate. The organic solution is washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (95:5 methyl-tert.-butyl ether:methanol) to yield Sanglifehrin C as a white amorphous powder. The latter consisted of a 4:1 mixture of Sanglifehrin C and its C53 epimer, Sanglifehrin C having the (S) configuration as depicted below (R=Me). ##STR53##

Workup

  1. customthe reaction is quenched with saturated aqueous sodium bicarbonate solution
  2. extractionThe resulting mixture is extracted twice with ethyl acetate
  3. washThe organic solution is washed twice with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (95:5 methyl-tert.-butyl ether:methanol)

Sources & evidence

ORD record
ord-b2187ee870934d4eb9930fc54d8ab738
Source dataset
uspto-grants-2000_09
Patent number
US06124453

Reaction notes

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