Glycine, N-methyl-, methyl ester, hydrochloride (1:1) → [(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl)-methyl-amino]-acetic Acid Methyl Ester

HRID 11700

반응식

HRID 11700 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH:9]=1)[CH:7]=O.Cl.[CH3:31][O:32][C:33](=[O:37])[CH2:34][NH:35][CH3:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:31][O:32][C:33](=[O:37])[CH2:34][N:35]([CH2:7][C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:10][CH2:11][C:12]([N:14]1[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:16][C@H:15]1[CH3:29])=[O:13])[CH3:36]

참가 물질

5

반응물 3

HCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 5049666Sodium triacetoxyborohydrideHCID 53673807(2R,5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

생성물 1

HCID 69655231[(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl)-methyl-amino]-acetic Acid Methyl Ester

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (0.10 g, 0.24 mmol) in methanol (2.5 ml) was added sarcosine methyl ester hydrochloride salt (0.10 g, 0.72 mmol) followed by sodium triacetoxyborohydride (0.155 g, 0.73 mmol). After 15 hours the solvent was removed and the resultant solid taken up in methylene chloride. After washing with pH 7 phosphate buffer (0.05 M) and saturated aqueous sodium chloride the organic layer was dried over magnesium sulfate. After filtration and concentration the title compound was isolated by chromatography on silica gel (0.051 g).

후처리

  1. customAfter 15 hours the solvent was removed
  2. washAfter washing with pH 7 phosphate buffer (0.05 M) and saturated aqueous sodium chloride the organic layer
  3. dry with materialwas dried over magnesium sulfate
  4. filtrationAfter filtration and concentration the title compound
  5. customwas isolated by chromatography on silica gel (0.051 g)

출처 및 근거

ORD 기록
ord-bc9c26b9cc494c06af51d41a336564d4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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