p-Toluenesulfonic acid monohydrate → HCID 54077611, compound

HRID 1656291Notes

Reaction equation

HRID 1656291 reaction equation
C([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19](O)([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8](C(C)=CC2CCC(OC3C=C4C(=CC=3)N(C)C=C4CCO[Si](C(C)(C)C)(C)C)C(OC)C2)[CH:7]([CH3:74])[CH:6](O)[CH2:5][C:4]1=[O:76])C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.CO>[CH3:33][O:32][CH:24]1[CH:23]2[O:34][CH:19]([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH2:8][CH:7]([CH3:74])[CH2:6][CH2:5][C:4](=[O:76])[CH2:3][CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 131718225HCID 131718225, compound

Product 1

HCID 54077611HCID 54077611, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-(1-methyl-3-(2-t-butyldimethylsilyloxyethyl)indol-5-yl)oxy-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 (200 mg.) in CH2Cl2 (6 mL.) and CH3OH (6 mL.) was added p-toluenesulfonic acid monohydrate (30 mg.). The reaction mixture was allowed to stir 3 hours. The reaction was quenched with saturated aqueous NaHCO3 and extracted 4× with CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The product was purified by preparative TLC on silica gel (1:1 hexanes/acetone) and again (7% CH3OH/CH2Cl2) giving -(4"-(1-methyl-3-(2-hydroxyethyl)indol-5-yl)oxy-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.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted 4× with CH2Cl2
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by preparative TLC on silica gel (1:1 hexanes/acetone) and again (7% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-ace9efdf24694909afd386cc1c77030f
Source dataset
uspto-grants-1993_10
Patent number
US05252732

Reaction notes

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