Sodium Bicarbonate → HCID 54522046, 화합물

HRID 582394노트

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HRID 582394 반응식
[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]

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 13689668N-Methyl-D-phenylalaninamideHCID 51356832HCID 51356832, 화합물

생성물 1

HCID 54522046HCID 54522046, 화합물수율 30.9%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-1bc03464b4084cd2bab60d5233a61467
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922770

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