Pyridine → HCID 57250718, compound

HRID 487832Notes

Reaction equation

HRID 487832 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](OC)[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(O)[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.S(Cl)([Cl:60])=O.N1C=CC=CC=1.[C:68](=[O:71])([O-])O.[Na+]>ClCCl>[CH2:35]([CH:30]1[CH:31]=[C:32]([CH3:34])[CH2:33][CH:2]([CH3:1])[CH2:3][CH:4]([O:56][CH3:57])[CH:5]2[O:10][C:9]([Cl:60])([CH:8]([CH3:53])[CH2:7][CH:6]2[O:54][CH3:55])[C:11](=[O:12])[C:13](=[O:14])[N:15]2[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[C:21](=[O:22])[O:23][CH:24]([C:40]([CH3:51])=[CH:41][CH:42]2[CH2:43][CH2:44][CH:45]([OH:50])[CH:46]([O:71][CH3:68])[CH2:47]2)[CH:25]([CH3:39])[CH:26]([OH:38])[CH2:27][C:28]1=[O:29])[CH:36]=[CH2:37]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 445643TacrolimusHCID 516892Sodium Bicarbonate

Product 1

HCID 57250718HCID 57250718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of FR-900506 (500 mg) in dry dichloromethane (25 ml) was added dropwise over 1 minute to a stirred, cool (0° C.) solution of thionyl chloride (0.45 ml) and pyridine (1.11 ml) in dry dichloromethane (20 ml) under nitrogen. After 20 minutes, saturated aqueous sodium hydrogen carbonate solution was added and the mixture was stirred at room temperature for 20 minutes. The organic extract was then separated and washed with dilute aqueous hydrochloric acid (1M, 20 ml), water (20 ml) and brine (10 ml) before being dried (MgSO4), filtered and evaporated in vacuo to give the sub-title compound as an an oil (512 mg).

Workup

  1. extractionThe organic extract
  2. customwas then separated
  3. washwashed with dilute aqueous hydrochloric acid (1M, 20 ml), water (20 ml) and brine (10 ml)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-fa201ce0eef24398bc013aeff62b009a
Source dataset
uspto-grants-1994_03
Patent number
US05296489

Reaction notes

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