Oxalate → HCID 9983610, compound

HRID 1194970Notes

Reaction equation

HRID 1194970 reaction equation
[C:1]([O:5][C:6](=[O:10])[C@H:7]([CH3:9])[NH2:8])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C([O-])=O.[CH2:17]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][CH2:34][CH2:35][CH2:36][C:37](=O)[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:29][CH2:28]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>C(O)C.O.C(O)(=O)C>[C:1]([O:5][C:6](=[O:10])[C@H:7]([CH3:9])[NH:8][C@@H:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:36][CH2:35][CH2:34][CH2:33][CH:30]1[CH2:31][CH2:32][N:27]([C:25]([O:24][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:26])[CH2:28][CH2:29]1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 71081OxalateHCID 89016L-Alanine 1,1-dimethylethyl esterHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 13817563Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate

Product 1

HCID 9983610HCID 9983610, compoundYield 11.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 5 g of L-alanine tert-butyl ester.oxalate, 11 g of ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate, 1.6 g of sodium acetate, 1.2 g of acetic acid and 100 ml of ethanol is stirred at room temperature for 1 hour, and a solution of 1.9 g of sodium cyanoborohydride in 100 ml of ethanol is added dropwise to the mixture over a period of 4 hours. After stirring at room temperature overnight, 500 ml of water is added to the reaction mixture, and the mixture is extracted with 300 ml of ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is separated and purified by silica gel column chromatography (hexane:acetone=4:1), whereby the first fraction yields 1.7 g of N-[(R)-5-(1-benzyloxycarbonyl-4-piperidyl)-1-ethoxycarbonylpentyl]-L-alanine tert-butyl ester as a colorless oil.

Workup

  1. extractionthe mixture is extracted with 300 ml of ethyl acetate
  2. washThe extract is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is separated
  6. custompurified by silica gel column chromatography (hexane:acetone=4:1), whereby the first fraction

Sources & evidence

ORD record
ord-c2ef57ca6b304b38a1ca91723e3158d4
Source dataset
uspto-grants-1989_03
Patent number
US04816466

Reaction notes

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