Acetone Cyanohydrin → ((S)-2-Cyano-2-hydroxy-1-isopropyl-ethyl)-carbamic acid benzyl ester

HRID 363739Notes

Reaction equation

HRID 363739 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH:16]=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([N:20](CC)CC)C.CC(C)(O)C#N>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH:16]([OH:17])[C:18]#[N:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 11009915benzyl [(1S)-1-formyl-2-methylpropyl]carbamate

Product 1

HCID 18648816((S)-2-Cyano-2-hydroxy-1-isopropyl-ethyl)-carbamic acid benzyl esterYield 143%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing N-benzyloxycarbonyl-L-valinal 22.2 g, 0.094 mol) in methylene chloride (500 mL) and triethylamine (5.81 g, 8.0 mL, 0.057 mol) was added acetone cyanohydrin (24.23 g, 26.0 mL, 0.2847 mol). The reaction was allowed to stir at room temperature overnight and then concentrated under reduced pressure. The residue was taken up into ether and washed with brine (3X). The solvent was removed under reduced pressure and purified by column chromatography (silica gel; 1:2 acetone:hexane) to give 21.38 g (86.6%) of 3-(S)-[(benzyloxycarbonyl)amino]-2-hydroxy-4-methylpentanenitrile as a pale yellow oil; TLC Rf =0.33 (silica gel; 1:2 acetone:hexane).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with brine (3X)
  3. customThe solvent was removed under reduced pressure
  4. custompurified by column chromatography (silica gel; 1:2 acetone:hexane)

Sources & evidence

ORD record
ord-8a4ad7aa41334eed91ed83e16c72d7bd
Source dataset
uspto-grants-1999_02
Patent number
US05874585

Reaction notes

Loading…