Hydrochloric Acid → N-[4-Hydroxymethyl-2-(2-methylphenyl)benzoyl]methionine methyl ester

HRID 2121270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2121270
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:4]=1.[CH3:19][O:20][C:21](=[O:28])[C@H:22]([CH2:24][CH2:25][S:26][CH3:27])[NH2:23].Cl.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH3:19][O:20][C:21](=[O:28])[C@H:22]([CH2:24][CH2:25][S:26][CH3:27])[NH:23][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][OH:1])=[CH:4][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 757711-HydroxybenzotriazoleHCID 106339044-Hydroxymethyl-2-(2-methylphenyl)benzoic acid

Produkt 1

HCID 54396972N-[4-Hydroxymethyl-2-(2-methylphenyl)benzoyl]methionine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Hydroxymethyl-2-(2-methylphenyl)benzoic acid (69 g, 285 mmol), prepared as in example 1075E, L-methionine methyl ester.HCl (68.3 g, 342 mmol), 1-hydroxybenzotriazole (46.2 g, 342 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (65.6 g, 342 mmol) were dissolved at ambient temperature in DMF (700 mL). To this solution was added triethylamine (47.7 mL, 342 mmol) and the resulting thick slurry was stirred overnight at ambient temperature. The reaction was diluted with EtOAc (700 mL) and washed with water (2×1L), saturated NaHCO3 (2×500 mL), 1N H3PO4 (2×500 mL), and brine. Organic layer dried with Na2SO4, filtered, and concentrated in vacuo to produce a pale yellow solid (110 g, 100% crude yield). 1H(300 MHz, CDCl3) δ 7.93 (1H, m), 7.44 (1H, dd, J=8, 2 Hz), 7.40-7.20 (4H, m), 7.19 (1H, bs), 5.92 (1H, m), 4.78 (2H, s), 4.63 (1H, m), 3.66 (3H, s), 2.20-2.00 (8H, m), 1.87 (1H, m), 1.75 (1H, m), 1.60 (1H, m). m/e (ESI) 386 (MH−).

Aufarbeitung

  1. washwashed with water (2×1L), saturated NaHCO3 (2×500 mL), 1N H3PO4 (2×500 mL), and brine
  2. dry with materialOrganic layer dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto produce a pale yellow solid (110 g, 100% crude yield)

Quellen und Nachweise

ORD-Eintrag
ord-a109ff892af2449f93e60335b6630934
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693123B2

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