4-Iodobenzenesulfonyl chloride → HCID 54077611, compound

HRID 1656548Notes

Reaction equation

HRID 1656548 reaction equation
[CH3:1][C@H:2]1[CH2:33][C:32]([CH3:34])=[CH:31][C@@H:30](CC=C)[C:28](=[O:29])[CH2:27][C@H:26](O)[C@@H:25]([CH3:39])[C@@H:24](/C(/C)=C/[C@H]2C[C@@H](OC)[C@H](O)CC2)[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.IC1C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:57][O:56][CH:4]1[CH:5]2[O:10][CH:9]([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:20]([CH2:19][CH2:18][CH2:17][CH2:16]2)[C:21](=[O:22])[O:23][CH2:24][CH:25]([CH3:39])[CH2:26][CH2:27][C:28](=[O:29])[CH2:30][CH:31]=[C:32]([CH3:34])[CH2:33][CH:2]([CH3:1])[CH2:3]1

Participants

5

Reactant 2

HCID 73994-Iodobenzenesulfonyl chlorideHCID 445643Tacrolimus

Product 1

HCID 54077611HCID 54077611, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the FR-900506 substance (100.7 mg) in pyridine (3 ml) was added p-iodobenzenesulfonyl chloride (500 mg), and the mixture was stirred at room temperature for 36 hours. The solution was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogen carbonate, water and an aqueous sodium chloride. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure The residue was chromatographed on silica gel (developing solvent diethyl ether and hexane, 3:1 v/v) to give 17-allyl-1,14-dihydroxy-12-2-[4-(p-iodobenzenesulfonyloxy)-3-methoxycyclohexyl]-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (61 mg) and 17-allyl-1-hydroxy-12-[2-[4-(piodobenzenesulfonyloxy)-3-methoxycyclohexyl]-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacosa-14,18-diene-2,3,10,16-tetraone (12 mg), respectively.

Workup

  1. washwashed with a saturated aqueous sodium hydrogen carbonate, water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure The residue
  5. customwas chromatographed on silica gel (developing solvent diethyl ether and hexane, 3:1 v/v)

Sources & evidence

ORD record
ord-99eaa6db974c4e16bf04912eb5d904ef
Source dataset
uspto-grants-1993_10
Patent number
US05254562

Reaction notes

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