Sodium Bicarbonate → HCID 54522046, compound

HRID 582394Notes

Reaction equation

HRID 582394 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 54522046HCID 54522046, compoundYield 30.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-1bc03464b4084cd2bab60d5233a61467
Source dataset
uspto-grants-1999_07
Patent number
US05922770

Reaction notes

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