Lithium Hydroxide → 3-(3-Benzenesulfonyl-1H-indol-6-yl)-N-hydroxy-acrylamide

HRID 84196

Reaction equation

HRID 84196 reaction equation
C1C=CC(P([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)C2C=CC=CC=2)=CC=1.[H-].[Na+].[C:22]1([S:28]SC2C=CC=CC=2)C=CC=C[CH:23]=1.C1C=C(Cl)[CH:39]=[C:38]([C:43]([O:45]O)=O)C=1.[Li+].[OH-:48].[NH2:49][O:50]C1CCCCO1.C1CN([P+](ON2N=[N:81][C:76]3[CH:77]=[CH:78][CH:79]=[CH:80][C:75]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(O)(C(F)(F)F)=[O:91]>CO.CN(C=O)C.CCN(CC)CC.O.C(Cl)Cl>[C:14]1([S:28]([C:22]2[C:75]3[C:76](=[CH:77][C:78]([CH:39]=[CH:38][C:43]([NH:49][OH:50])=[O:45])=[CH:79][CH:80]=3)[NH:81][CH:23]=2)(=[O:91])=[O:48])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

14

Reactant 8

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 11776TriphenylphosphineHCID 13436Diphenyl disulfideHCID 24758Sodium hydrideHCID 70297m-Chloroperbenzoic acidHCID 2724699PyBOPHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamine

Product 1

HCID 760350453-(3-Benzenesulfonyl-1H-indol-6-yl)-N-hydroxy-acrylamide

Reagents, catalysts & solvents 5

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Compound 24 was synthesized via the route as shown in Scheme 5 above (reagents and conditions: (a) Ph3P═CH—CO2CH3, CH2Cl2; (b) NaH, Ph-S—S-Ph, DMF; (c) MCPBA, CH2Cl2; (d) LiOH, MeOH, H2O; (e) (i) NH2OTHP, PyBOP, NEt3, DMF; (ii) TFA, MeOH).

Sources & evidence

ORD record
ord-bb26cdb93aed4d7085b435cf27d4bef9
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Linked notes

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