Tacrolimus → 1,14-Dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-propyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

HRID 1651773Notes

Reaction equation

HRID 1651773 reaction equation
[CH3:1][C@H:2]1[CH2:33][C:32]([CH3:34])=[CH:31][C@@H:30]([CH2:35][CH:36]=[CH2:37])[C:28](=[O:29])[CH2:27][C@H:26]([OH:38])[C@@H:25]([CH3:39])[C@@H:24](/[C:40](/[CH3:51])=[CH:41]/[C@H:42]2[CH2:47][C@@H:46]([O:48][CH3:49])[C@H:45]([OH:50])[CH2:44][CH2:43]2)[O:23][C:21](=[O:22])[C@H:20]2[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]2)[C:13](=[O:14])[C:11](=[O:12])[C@:9]2([OH:52])[O:10][C@@H:5]([C@@H:6]([O:54][CH3:55])[CH2:7][C@H:8]2[CH3:53])[C@@H:4]([O:56][CH3:57])[CH2:3]1>C(OCC)(=O)C.[Pd]>[OH:52][C:9]12[O:10][CH:5]([CH:6]([O:54][CH3:55])[CH2:7][CH:8]1[CH3:53])[CH:4]([O:56][CH3:57])[CH2:3][CH:2]([CH3:1])[CH2:33][C:32]([CH3:34])=[CH:31][CH:30]([CH2:35][CH2:36][CH3:37])[C:28](=[O:29])[CH2:27][CH:26]([OH:38])[CH:25]([CH3:39])[CH:24]([C:40]([CH3:51])=[CH:41][CH:42]1[CH2:43][CH2:44][CH:45]([OH:50])[CH:46]([O:48][CH3:49])[CH2:47]1)[O:23][C:21](=[O:22])[CH:20]1[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]1)[C:13](=[O:14])[C:11]2=[O:12]

Participants

4

Reactant 1

HCID 445643Tacrolimus

Product 1

HCID 571132511,14-Dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-propyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the FR-900506 substance (50 mg) in ethyl acetate (2 ml) was subjected to catalytic reduction using 10% palladium on carbon (10 mg) under atmospheric pressure at room temperature for 20 minutes. The reaction mixture was filtered and the filtrate was evaporated to dryness, which was purified on thin layer chromatography. Development with a mixture of chloroform and acetone (5:1 v/v) gave 1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-propyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (50.0 mg).

Workup

  1. customat room temperature
  2. customfor 20 minutes
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated to dryness, which
  5. customwas purified on thin layer chromatography
  6. additionDevelopment with a mixture of chloroform and acetone (5:1 v/v)

Sources & evidence

ORD record
ord-12471841850349a9bbdd9e3594bbe30c
Source dataset
uspto-grants-1990_05
Patent number
US04929611

Reaction notes

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