L-Alanine methyl ester → HCID 131723866, compound

HRID 1267208Notes

Reaction equation

HRID 1267208 reaction equation
[CH3:1][CH:2]([CH3:15])[C@H:3]([O:6][CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:4]=O.[NH2:16][C@H:17]([C:19]([O:21][CH3:22])=[O:20])[CH3:18].C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO>[CH3:15][CH:2]([CH3:1])[C@H:3]([O:6][CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:12])([CH3:13])[CH3:14])[CH2:4][NH:16][C@H:17]([C:19]([O:21][CH3:22])=[O:20])[CH3:18]

Participants

6

Reactant 4

HCID 82335L-Alanine methyl esterHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 20578888HCID 20578888, compound

Product 1

HCID 131723866HCID 131723866, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-methyl-2-(S)-(2-trimethylsilylethyloxy)methyloxybutanal (1.0 eq) was stirred in methanol at room temperature with L-Alanine, methyl ester (0.8 eq; Bachem). Sodium cyanoborohydride (0.5 eq) was added to the solution, and the reaction was stirred for 17 hours. The reaction was made alkaline by addition of aqueous saturated NaHCO3 solution. The mixture was extracted with dichloromethane, dried over sodium sulfate, and concentrated in vacuo. The residue was purified via radial chromatography using 20% ethyl acetate in hexanes to afford the title intermediate as a colorless oil.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified via radial chromatography

Sources & evidence

ORD record
ord-cc7dcb8d4a8c4d36a43e1b77bbce4ea8
Source dataset
uspto-grants-2003_04
Patent number
US06552013B1

Reaction notes

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