HCID 131724592, compound → HCID 178476994, compound

HRID 1006770Notes

Reaction equation

HRID 1006770 reaction equation
[CH2:1]([O:8]C(=N)C(Cl)(Cl)Cl)[C:2]1C=CC=CC=1.C([S:19](O)(=O)=O)(F)(F)F.[C:23]1([OH:29])C=CC=C[CH:24]=1.[CH:30]1[CH:35]=[CH:34][C:33]([P:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:32][CH:31]=1.[CH3:49][CH:50]([O:52][C:53](/[N:55]=[N:56]/[C:57]([O:59][CH:60]([CH3:62])[CH3:61])=[O:58])=[O:54])[CH3:51]>CS(C)=O.C(Cl)Cl.C1CCCCC1.CCO.O1CCOCC1.C1COCC1.[Pd].[H][H]>[C:1]([O-:8])(=[S:19])[CH3:2].[CH3:24][C:23]([SH:19])=[O:29].[CH:46]1[CH:45]=[CH:44][C:43]([P:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:33]2[CH:34]=[CH:35][CH:30]=[CH:31][CH:32]=2)=[CH:48][CH:47]=1.[CH3:62][CH:60]([O:59][C:57](/[N:56]=[N:55]/[C:53]([O:52][CH:50]([CH3:51])[CH3:49])=[O:54])=[O:58])[CH3:61]

Participants

9

Reactant 2

HCID 131724592HCID 131724592, compoundHCID 178459889HCID 178459889, compound

Product 2

HCID 178476994HCID 178476994, compoundHCID 178477101HCID 178477101, compound

Reagents, catalysts & solvents 5

HCID 178506449HCID 178506449, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×HCID 21916607Dichloromethane cyclohexaneSolventHCID 22560076Dioxan ethanolSolvent

Procedure

In case R2Y is R2O: Compounds of this type may be obtained by reaction shown in step f and g. These reaction may comprise (step f) reaction of compounds 4 with R2Br/NaH in DMSO at room temperature or benzyl-2,2,2-trichloroacetimidate/CF3SO3H in CH2Cl2/cyclohexane at room temperature (here the R2-side chains may be manipulated by reaction with 10% Pd/C/H2 in EtOH/dioxane) or the reaction is performed with PhOH/Ph3P/DIAD in THF at room temperature. All reactions may be followed by removal of the t-Bu-ether in TFA at 0° C. to room temperature. For the preparation of compounds of formula 7 (step g) compounds 6 (if m=0: for inversion of the configuration) may be obtained by thioacetate formation under Mitsunobu conditions (e.g. CH3COSH/Ph3P/DIAD in THF at 0° C. to room temperature) followed by formation of the thiol (e.g. by reaction with MeONa in MeOH at 0° C.; plus potential side chain manipulation with 1 N Na2CO3 in MeOH) or (if m=0: for retention of configuration) reaction of compounds 6 for e.g. formation of the mesylate (MeSO3H/Et3N/Ph3P/DIAD in toluene at 0° C. to 85° C.) followed by preparation of the thioacetate (e.g. KSCOCH3 in DMF at 100° C.) and formation of the thiol (MeONa in MeOH at 0° C.).

Workup

  1. customCompounds of this type may be obtained by reaction
  2. customThese reaction
  3. customAll reactions may be followed by removal of the t-Bu-ether in TFA at 0° C. to room temperature
  4. customFor the preparation of compounds of formula 7 (step g) compounds 6 (if m=0

Sources & evidence

ORD record
ord-b5c2560a7cf14a8794ace7ea51ee3d3d
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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