Potassium Hydroxide → Methyl alpha-methyl-D-tryptophanate

HRID 2396428

반응식

HRID 2396428 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].[OH-].[K+]>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

4

반응물 2

HCID 14797Potassium HydroxideHCID 6923821HCID 6923821, 화합물

생성물 1

HCID 6923819Methyl alpha-methyl-D-tryptophanate수율 13,099.4%

시약·촉매·용매 1

HCID 24243Trisodium Phosphate용매

실험 절차

To a suspension of (±)-α-methyltryptophan methyl ester (79.5 mg, 0.342 mmol) in 30 mL of 50 mM sodium phosphate buffer pH 7.5 was added carboxypeptidase W (3.0 mg of solid). The resulting suspension was stirred at ambient temperature. After 6.5 h, 56% conversion was observed by HPLC (C18 column, 280 nm detection, amino acid tR =8.2 min and amino ester tR =11.1 min). The reaction was adjusted to pH 12 by the addition of 2 N KOH and then extracted with 1×15 and 1×20 mL ethyl acetate. The combined extracts were treated with brine, dried with magnesium sulfate, then concentrated in vacuo to yield (R)-α-methyltryptophan methyl ester (10.4 mg, 44.8 mmol, 13.1%). The enantiomeric excess of the unreacted amino ester was determined by chiral HPLC (Uttron ES-OVM column from Shinwa Chemical Industries, Ltd., 280 nm, (R)-enantiomer tR =13.7 min and (S)-enantiomer tR =18.8 min) to be 89.9% (r)-enantiomer.

후처리

  1. extractionextracted with 1×15 and 1×20 mL ethyl acetate
  2. additionThe combined extracts were treated with brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4e5fec69a8a746ad8c97f86ec91825f8
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05492830

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