HCID 6923821, 화합물 → Methyl alpha-methyl-D-tryptophanate

HRID 2396427

반응식

HRID 2396427 반응식
[CH3:1][O:2][C:3](=[O:17])[C@:4]([CH3:16])([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5]>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[CH3:1][O:2][C:3](=[O:17])[C@@:4]([CH3:16])([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5]

참가 물질

3

반응물 1

HCID 6923821HCID 6923821, 화합물

생성물 1

HCID 6923819Methyl alpha-methyl-D-tryptophanate수율 10,402.5%

시약·촉매·용매 1

HCID 24243Trisodium Phosphate용매

실험 절차

To a suspension of (±)-α-methyltryptophan methyl ester (150.0 mg, 0.646 mmol) in 50 mL of 50 mM sodium phosphate buffer pH 7.5 was added carboxypeptidase Y from Bakers Yeast (6.4 mg). The resulting suspension was stirred at ambient temperature. After 4 h, 75% conversion was observed by HPLC (C18 column, 254 nm detection, acid tR =9.0 min and ester tR =11.9 min). The reaction was extracted with 2×25 mL chloroform. The combined extracts were treated with brine, dried with magnesium sulfate, then concentrated in vacuo to yield (R)-α-methyltryptophan methyl ester (15.6 mg, 67.2 mmol, 10.4%). A portion of this α-methyl amino ester was derivatized with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (TAGIT). HPLC analysis of the resulting thioureas showed the (R,S)-diastereomer to be in >99% diastereomeric excess (C18 column, 254 nm detection, S,S)-diastereomer tR =15.9 min and (R,S)-diastereomer tR =16.8 min).

후처리

  1. additionwas added carboxypeptidase Y from Bakers Yeast (6.4 mg)
  2. extractionThe reaction was extracted with 2×25 mL chloroform
  3. additionThe combined extracts were treated with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9c71beaed8264b348facb4cab7b20ba6
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05492830

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