Triethylamine → tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoate

HRID 25686

Reaction equation

HRID 25686 reaction equation
[C:1]([O:5][C:6](=[O:14])[C@@H:7]([NH2:13])[C@@H:8]([OH:12])[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:22]([O:29][C:30](ON1C(=O)CCC1=O)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][C:30]([NH:13][C@@H:7]([C@@H:8]([OH:12])[CH:9]([CH3:10])[CH3:11])[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:14])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 15408106(2S,3S)-2-amino-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

Product 1

HCID 59065895tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S,3S)-2-amino-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester (297 mg, 1.37 mmol) and triethylamine (139 mg, 1.37 mmol) in anhydrous methylene chloride (2 ml) was cooled to 0° C. under a nitrogen atmosphere. To this solution was added N-(benzyloxycarbonyloxy)-succinimide (343 mg, 1.37 mmol). The resulting mixture was warmed to room temperature and stirred for 15 hours. The reaction mixture was partitioned between ether and water. The organic layer was washed with cold 1N hydrochloric acid and saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo, to provide tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]-amino}-3-hydroxy-4-methylpentanoate (445 mg, 96%) as a yellow oil.

Workup

  1. customThe reaction mixture was partitioned between ether and water
  2. washThe organic layer was washed with cold 1N hydrochloric acid and saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8d8c4522a1b4656b2cd8f3b4927d4b2
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Linked notes

Loading…