Hydrochloric Acid → 5-Methoxy-benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-6-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide

HRID 229788

Reaktionsgleichung

Reaktionsgleichung von HRID 229788
C([O:5][C:6](=O)[NH:7][C@H:8]([C:13](=[O:33])[NH:14][CH:15]1[CH2:21][CH:20]([CH3:22])[CH2:19][N:18]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)(=[O:25])=[O:24])[CH2:17][CH:16]1[OH:32])[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.Cl.O1CCOCC1.Cl.[CH3:43][O:44][C:45]1[CH:46]=[CH:47][C:48]2[O:52][C:51](C(O)=O)=[CH:50][C:49]=2[CH:56]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>>[OH:32][CH:16]1[CH:15]([NH:14][C:13]([C@@H:8]([NH:7][C:6]([C:51]2[O:52][C:48]3[CH:47]=[CH:46][C:45]([O:44][CH3:43])=[CH:56][C:49]=3[CH:50]=2)=[O:5])[CH2:9][CH:10]([CH3:11])[CH3:12])=[O:33])[CH2:21][CH:20]([CH3:22])[CH2:19][N:18]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)(=[O:25])=[O:24])[CH2:17]1

Komponenten

7

Edukt 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 2886385-Methoxybenzofuran-2-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11496976{(S)-1-[3-hydroxy-6-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl esterHCID 204431481,4-Dioxane hydrochloride

Produkt 1

HCID 866074165-Methoxy-benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-6-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amideAusbeute 69 %

Versuchsvorschrift

To {(S)-1-[3-hydroxy-6-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester (0.13 g, 0.28 mmol) was added HCl/dioxane (4M, 2.8 ml, 11.2 mmol). The mixture was stirred at RT for 2 h before solvents and excess amount of HCl was removed on rotavapor. The result white solid was dissolved in 5 ml DMF. To the solution was added 5-methoxy-benzofuran-2-carboxylic acid (63.4 mg, 0.33 mmol), HBTU (125 g, 0.33 mmol) and NMM (0.14 g, 1.34 mmol). The mixture was stirred at RT overnight. DMF was then removed and the residue was re-dissolved in EtOAc (50 ml), washed with 10% NaHCO3 (50 ml×2) and brine (50 ml). The combined organics were concentrated by rotary evaporation. Purification by column chromatograghy gave the title compound (110 mg in 69% yield, 2 steps): MS (M+H+):573.4; 1H-NMR (400 Hz, CDCl3): d=8.74-8.66(dd, 1H), 7.96-6.97(m, 9H), 4.72(m, 1H), 4.18-3.21(m, 7H), 2.81(m, 1H), 2.04-1.74(m, 6H), 1.25(m, 2H), 0.99-0.87(m, 9H)

Aufarbeitung

  1. customwas removed on rotavapor
  2. dissolutionThe result white solid was dissolved in 5 ml DMF
  3. customDMF was then removed
  4. dissolutionthe residue was re-dissolved in EtOAc (50 ml)
  5. washwashed with 10% NaHCO3 (50 ml×2) and brine (50 ml)
  6. concentrationThe combined organics were concentrated by rotary evaporation
  7. customPurification by column chromatograghy

Quellen und Nachweise

ORD-Eintrag
ord-8bb701dc1d4a4713a1bb87f39fee1c71
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563784B2

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