Hydrochloric Acid → (S)-2-Amino-3-[4-(5-methoxy-2-methyl-3-oxo-2,3-di hydro-pyridazin-4-yl)-phenyl]-propionic acid

HRID 1435942노트

반응식

HRID 1435942 반응식
B([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)(O)O.Br[C:17]1[C:18](=[O:26])[N:19]([CH3:25])[N:20]=[CH:21][C:22]=1[O:23][CH3:24].C(=O)([O-])[O-].[Na+].[Na+].Cl>CC#N.CO>[NH2:10][C@@H:9]([CH2:8][C:7]1[CH:14]=[CH:15][C:4]([C:17]2[C:18](=[O:26])[N:19]([CH3:25])[N:20]=[CH:21][C:22]=2[O:23][CH3:24])=[CH:5][CH:6]=1)[C:11]([OH:13])=[O:12]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 150315L-p-BoronophenylalanineHCID 106326414-Bromo-5-methoxy-2-methylpyridazin-3(2H)-one

생성물 1

HCID 11536782(S)-2-Amino-3-[4-(5-methoxy-2-methyl-3-oxo-2,3-di hydro-pyridazin-4-yl)-phenyl]-propionic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

실험 절차

4-Borono-L-phenylalanine (0.30 g, 1.0 mmol), 4-Bromo-5-methoxy-2-methyl-2H-pyridazin-3-one (0.35 g, 1.0 mmol), tetrakistriphenylphosphine palladium(0) (0.09 g), and 2.0 M aqueous sodium carbonate (3.0 mL) were refluxed in MeCN (900 mL) for 4 d. The mixture was acidified with 2.0 N HCl and treated with MeOH. The solid was filtered off and the mixture was concentrated in vacuo. The crude solid was purified using a Gilson HPLC containing a Kromasil column (10 u, 100 Å C18, column length 250×50 mm, gradient 100:0 to 10:90 H2O:MeCN) to give 2-(S)-Amino-3-[4-(5-methoxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid. MS (ES+) 304.

후처리

  1. filtrationThe solid was filtered off
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe crude solid was purified
  4. additioncontaining a Kromasil column (10 u, 100 Å C18, column length 250×50 mm, gradient 100:0 to 10:90 H2O:MeCN)

출처 및 근거

ORD 기록
ord-6fed558ce0dc47e893981ac45e528931
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618983B2

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