Cycloleucine → 1-(((Phenylmethoxy)carbonyl)amino)cyclopentanecarboxylic acid

HRID 653181Notes

Reaction equation

HRID 653181 reaction equation
[NH2:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:30]([NH:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1)([O:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:31]

Participants

5

Reactant 3

HCID 2901CycloleucineHCID 10387Benzyl chloroformateHCID 6913588N,O-bis(trimethylsilyl)acetamide

Product 1

HCID 15126351-(((Phenylmethoxy)carbonyl)amino)cyclopentanecarboxylic acidYield 911.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 12.9 g (0.010 mole) of 1-amino-1-cyclopentane carboxylic acid in 500 ml of methylene chloride is added 25 ml (0.10 mole) of N,O-bis(trimethylsilyl)acetamide. The mixture is stoppered and stirred at room temperature for 3 days, whereupon complete solution is obtained. 17 g (0.10 mole) of benzylchloroformate is added and the mixture stirred for an additional 1 hour. It is then washed with 300 ml each 2N HCl, water and saturated brine and dried over sodium sulfate. Filtration, evaporation and trituration with hexane gives 24 g of 1-carbobenzoxyamino-1-cyclopentane carboxylic acid, mp. 93°-5° C. 5.3 g (0.020 mole) of 1-carbobenzoxyamino-1-cyclopentane carboxylic acid is dissolved in 100 ml dimethylformamide and 3.1 g (0.020 mole) of 1-hydroxybenzotriazole hydrate and 2.5 g (0.020 mole) of 1,3-diisopropylcarbodiimide are added. The mixture is stirred at room temperature for three hours and 1.8 g (0.020 mole) of 4-amino-1-butanol is added. Stirring at room temperature is continued for 24 hours. The solvent is removed in vacuo and replaced with 500 ml of methylene chloride. The mixture is washed with 2N HCl, saturated sodium bicarbonate solution and water and dried over sodium sulfate. Filtration and evaporation gives 6.7 g of 1-carbobenzoxyamino-1-cyclopentane carboxylic acid, 4-hydroxybutylamide, m.p 117°-8° C.

Workup

  1. customis obtained
  2. stirringthe mixture stirred for an additional 1 hour
  3. washIt is then washed with 300 ml each 2N HCl, water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration, evaporation and trituration with hexane

Sources & evidence

ORD record
ord-0a264f4e631548558fc086ff3bfce5d4
Source dataset
uspto-grants-1987_06
Patent number
US04675403

Reaction notes

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