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

HRID 2242623Notes

Reaction equation

HRID 2242623 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([S:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]([CH2:22][NH2:23])[CH2:17][CH2:16][CH2:15]3)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[CH2:24]([O:31][C:32]([N:34]([CH2:36][C:37](O)=[O:38])[CH3:35])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.ON1C2C=CC=CC=2N=N1.CC[N+](CCCN(C)C)=C=N.C(N(CC)CC)C>C(Cl)Cl>[CH2:24]([O:31][C:32](=[O:33])[N:34]([CH2:36][C:37](=[O:38])[NH:23][CH2:22][CH:18]1[C:19]2[C:14](=[CH:13][C:12]([S:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=3)(=[O:11])=[O:10])=[CH:21][CH:20]=2)[CH2:15][CH2:16][CH2:17]1)[CH3:35])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 97053N-CarbobenzoxysarcosineHCID 218833923-(Dimethylamino)propyl-ethyl-(iminomethylidene)azaniumHCID 66651558C-[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-methylamine hydrochloride

Product 1

HCID 66651708({[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl)-methyl-carbamic acid benzyl esterYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

C-[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-methylamine hydrochloride (0.2 gms, 0.56 mmole), (Benzyloxycarbonyl-methyl-amino)-acetic acid (0.15 gms, 0.67 mmole), 1-hydroxybenzotriazole (0.11 gms, 0.84 mmole), 0.16 gms N-(3-dimethylaminopropyl)-N-ethylcarbodiimide (0.16 gms, 0.84 mmole) and triethylamine (0.50 ml, 3.36 mmole) in 30 mL methylene chloride and was stirred at room temperature for 24 hours. The reaction was quenched with 0.2 ml water, and the entire mixture was absorbed on to silica gel and medium pressure chromatography, eluting with ethyl acetate, gave 0.15 gms of ({[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl)-methyl-carbamic acid benzyl ester as an oil.

Workup

  1. customThe reaction was quenched with 0.2 ml water
  2. customthe entire mixture was absorbed on to silica gel and medium pressure chromatography
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-03fc706db3b5422db1c3b483f979c811
Source dataset
uspto-grants-2010_03
Patent number
US07671235B2

Reaction notes

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