2-Amino-3,3-dimethylbutanoic acid → D-tert-leucine

HRID 76844

반응식

HRID 76844 반응식
[NH2:1][CH:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4].O.C([C@](C(O)=O)(O)[C@](C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1>O>[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4]

참가 물질

4

반응물 2

HCID 3061312-Amino-3,3-dimethylbutanoic acidHCID 122598382Dibezoyl-D-tartaric acid monohydrate

생성물 1

HCID 6950340D-tert-leucine수율 92%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
28 °C

실험 절차

(DL)-tert-Leucine (15 g, 0.1145 mol) was dissolved in water (180 mL). To the solution was added dibenzoyl-d-tartaric acid monohydrate (21.5 g, 0.057 mol) and stirred for 24 hours at 28° C. (±3). The reaction mixture was filtered to collect L-tert-leucine dibenzoyl-d-tartrate salt. The filtrate was reserved for isolating D-tert-leucine later. The tartrate salt was added to water (150 mL) followed by concentrated sulphuric acid (3 mL) and stirred for 4 hours. Liberated dibenzoyl-d-tartaric acid was collected and dried (19.8 g, 92% yield). The filtrate was washed with diisopropyl ether (50 mL) to remove any traces of dibenzoyl-d-tartaric acid, cooled to 5° C. and treated with a saturated solution of barium hydroxide till the pH was neutral. It was filtered to remove the precipitated barium sulphate. The filtrate was concentrated under reduced pressure to remove all the solvent. The residue obtained was stirred with acetone (15 mL×2), filtered and dried to obtain colorless solid L-tert-leucine (6 g, 80% yield, 99% chemical purity, 99.9% chiral purity).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customto collect L-tert-leucine dibenzoyl-d-tartrate salt

출처 및 근거

ORD 기록
ord-ddb0d8bc251843a794ab7a67a49c4307
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835676B2

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