Sodium Bicarbonate → HCID 54522046、化合物

HRID 582394ノート

反応式

HRID 582394 の反応式
[CH3:1][NH:2][C:3](=[O:13])[C@@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].[C:14]([O:18][C:19](=[O:35])[NH:20][C@@H:21]([CH:33]=O)[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)([CH3:17])([CH3:16])[CH3:15].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.O.C(O)(=O)C>[C:14]([O:18][C:19](=[O:35])[NH:20][C@@H:21]([CH2:33][NH:5][C@@H:4]([C:3](=[O:13])[NH:2][CH3:1])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)([CH3:17])([CH3:15])[CH3:16]

参加物

8

反応物 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 13689668N-Methyl-D-phenylalaninamideHCID 51356832HCID 51356832、化合物

生成物 1

HCID 54522046HCID 54522046、化合物収率 30.9%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

D-Phenylalanine-N-methyl amide (1.50 g, 8.35 mmol) and (1R)-1-formyl-2-(2-naphthyl)ethylcarbamic acid tert-butyl ester (2.50 g, 8.35 mmol) were dissolved in methanol (40 ml). Molsieves (3 Å, 30 g) and acetic acid (3 ml) were added and the mixture was cooled with ice and sodium cyanoborohydride (0.80 g, 12.5 mmol) was added. The mixture was stirred overnight at room temperature. Water (30 ml) and saturated aqueous sodium hydrogen carbonate (30 ml) were added and the mixture was extracted with methylene chloride (3×40 ml). The combined organic phases were dried (magnesium sulfate) and the solvent was removed in vacuo. The residue was chromatographed on silica (3×30 cm) using ethyl acetate/heptane (1:1) as eluent to afford 1.19 g of ((1R)-1-(((1R)-1-methylcarbamoyl-2-phenylethylamino)methyl)-2-(2-naphthyl)ethyl)carbamic acid tert butyl ester

後処理

  1. additionwas added
  2. extractionthe mixture was extracted with methylene chloride (3×40 ml)
  3. dry with materialThe combined organic phases were dried (magnesium sulfate)
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed on silica (3×30 cm)

出典と根拠

ORDレコード
ord-1bc03464b4084cd2bab60d5233a61467
出典データセット
uspto-grants-1999_07
特許番号
US05922770

反応ノート

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