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DL-leucine → L-leucine N-carbobenzoxy-L-aspartic acid

HRID 64788
Notes
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Reaction equation

HRID 64788 reaction equation
[NH2:1][CH:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[C:10]([NH:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][C:23]([OH:25])=[O:24])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].S(=O)(=O)(O)O>O>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[C:10]([NH:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][C:23]([OH:25])=[O:24])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 857DL-leucineHCID 1118Sulfuric AcidHCID 2723942N-(Benzyloxycarbonyl)aspartic acid

Product 1

HCID 70458343L-leucine N-carbobenzoxy-L-aspartic acidYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Ten grams of DL-leucine, 12.2 g of N-carbobenzoxy-L-aspartic acid and 1.9 g of sulfuric acid were added to 500 ml of water and the resulting solution was heated to 60° C. This solution was cooled to 10° C. at a rate of 2° C. per hour while stirring, and was stirred for another two hours. The resulting crystal was separated, washed with 30 ml of water and dried to give 9.1 g of an L-leucine/N-carbobenzoxy-L-aspartic acid. Analysis showed that the optical purity of the L-leucine was 95%.

Workup

  1. temperatureThis solution was cooled to 10° C. at a rate of 2° C. per hour
  2. stirringwas stirred for another two hours
  3. customThe resulting crystal was separated
  4. washwashed with 30 ml of water
  5. customdried

Sources & evidence

ORD record
ord-80bd70f61956487b962e5c35298033de
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04610827

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes