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

HRID 971301

Reaktionsgleichung

Reaktionsgleichung von HRID 971301
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

Komponenten

7

Edukt 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

Produkt 1

HCID 66651708({[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl)-methyl-carbamic acid benzyl esterAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-94adb9c77a1a4f6099fb3fb8da2f1a5a
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312359B2

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