Acetic Acid → HCID 86595999, 화합물

HRID 547275노트

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HRID 547275 반응식
[C:1]([O:5][C:6](=[O:21])[CH2:7][CH2:8][NH:9][CH2:10][C:11]1[C:12]([Cl:20])=[N:13][C:14]([C:17](=O)[CH3:18])=[CH:15][CH:16]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:23]1[CH:31]=[CH:30][C:26]([CH2:27][O:28][NH2:29])=[CH:25][C:24]=1[C:32]([F:35])([F:34])[F:33].[C:36](O)(=O)[CH3:37]>CO>[C:1]([O:5][C:6](=[O:21])[CH2:7][CH2:8][NH:9][CH2:10][C:11]1[C:12]([Cl:20])=[N:13][C:14]([C:17](=[N:29][O:28][CH2:27][C:26]2[CH:30]=[CH:31][C:23]([CH:37]3[CH2:36][CH2:15][CH2:16][CH2:11][CH2:10]3)=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:25]=2)[CH3:18])=[CH:15][CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 67189157O-(4-chloro-3-trifluoromethyl-benzyl)-hydroxylamineHCID 865959983-[(6-Acetyl-2-chloro-pyridin-3-ylmethyl)-amino]-propionic acid tert-butyl ester

생성물 1

HCID 86595999HCID 86595999, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 3-[(6-acetyl-2-chloro-pyridin-3-ylmethyl)-amino]-propionic acid tert-butyl ester (1 eq) in methanol is added O-(4-chloro-3-trifluoromethyl-benzyl)-hydroxylamine (1 eq) followed by the addition of acetic acid (0.05 eq). The mixture is stirred at room temperature for 5 hours. After concentration, the residue is purified by column chromatography to give 3-({2-chloro-6-[1-(4-cyclohexyl-3-trifluoromethyl-benzyloxyimino)-ethyl]-pyridin-3-ylmethyl}-amino)-propionic acid tert-butyl ester. MS: (ES+) 568.3 (M+1)+. The tert-butyl group is subsequently removed by treatment with TFA/DCM (1/1) at room temperature. The final compound 3-({2-chloro-6-[1-(4-cyclohexyl-3-trifluoromethyl-benzyloxyimino)-ethyl]-pyridin-3-ylmethyl}-amino)-propionic acid is purified by preparative LCMS. 1H NMR (400 MHz, CD3OD) δ 1.28-1.60 (m, 5H), 1.71-1.92 (m, 5H), 2.30 (s, 3H), 2.79 (t, 2H), 2.90 (m, 1H), 3.38 (t, 2H), 4.42 (s, 2H), 5.29 (s, 2H), 7.38 (d, 1H), 7.50-7.68 (m, 3H), 7.94 (s, 2H). MS: (ES+): 512.2 (M+1)+.

후처리

  1. concentrationAfter concentration
  2. customthe residue is purified by column chromatography

출처 및 근거

ORD 기록
ord-4c01375616c7407d9adec9a423b66ef0
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939519B2

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