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

反応式

HRID 11700 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bc9c26b9cc494c06af51d41a336564d4
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

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