({[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl)-methyl-carbamic acid benzyl ester → n-[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-2-methylamino-acetamide formate salt

HRID 420208Notes

Reaction equation

HRID 420208 reaction equation
C([O:8][C:9](=[O:37])[N:10]([CH2:12][C:13](=[O:36])[NH:14][CH2:15][CH:16]1[C:25]2[C:20](=[CH:21][C:22]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)(=[O:28])=[O:27])=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1)C)C1C=CC=CC=1>CO.C(O)=O.[Pd]>[CH:9]([OH:37])=[O:8].[F:35][C:31]1[CH:30]=[C:29]([S:26]([C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[CH:16]([CH2:15][NH:14][C:13](=[O:36])[CH2:12][NH:10][CH3:9])[CH2:17][CH2:18][CH2:19]3)(=[O:28])=[O:27])[CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 1

HCID 66651708({[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl)-methyl-carbamic acid benzyl ester

Product 1

HCID 66651472n-[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-2-methylamino-acetamide formate saltYield 144.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

To a stirring solution of ({[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl)-methyl-carbamic acid benzyl ester (0.15 g) in 20 ml methanol and 2 ml formic acid at room temperature was added 0.1 gms of 10% palladium on carbon. After stirring for three hours the mixture was filtered thru Celite and the clear filtrate was concentrated to dryness. The residue was recrystallized from ethyl acetate and diethyl ether to give 0.090 gms of N-[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-2-methylamino-acetamide formate salt: M+H=391.

Workup

  1. filtrationwas filtered thru Celite
  2. concentrationthe clear filtrate was concentrated to dryness
  3. customThe residue was recrystallized from ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-dedf745c1de94c789d5edb592cb914a6
Source dataset
uspto-grants-2012_01
Patent number
US08093424B2

Reaction notes

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