Dl-Phenylalanine → L-phenylalanine N-carbobenzoxy-L-aspartic acid

HRID 64783

반응식

HRID 64783 반응식
[NH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]([NH:23][C@H:24]([C:29]([OH:31])=[O:30])[CH2:25][C:26]([OH:28])=[O:27])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].S(=O)(=O)(O)O.[OH-].[Na+].N[C@@H](C(O)=O)CC1C=CC=CC=1>O>[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]([NH:23][C@H:24]([C:29]([OH:31])=[O:30])[CH2:25][C:26]([OH:28])=[O:27])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

참가 물질

7

반응물 5

HCID 994Dl-Phenylalanine2회HCID 1118Sulfuric Acid4회HCID 14798Sodium HydroxideHCID 71567D-PhenylalanineHCID 2723942N-(Benzyloxycarbonyl)aspartic acid

생성물 1

HCID 13714282L-phenylalanine N-carbobenzoxy-L-aspartic acid수율 50.7%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

Eight grams of DL-phenylalanine, 10 g of N-carbobenzoxy-L-aspartic acid and 2.4 g of sulfuric acid were dissolved in 90 ml of water. A 10% aqueous solution (9.7 ml) of caustic soda was added to the resulting solution over six hours while it was continuously stirred at 50° C. As a result, half of the sulfuric acid was neutralized, and the molar amount of the remaining sulfuric acid was a quarter of the amount of DL-phenylalanine. (It will be noted that in the other examples also, the amount of sulfuric acid was adjusted to be one mol per 2 mols of the finally present D-phenylalanine.) The resulting crystal was separated, washed with 10 ml of water and dried to give 8.2 g of L-phenylalanine/N-carbobenzoxy-L-aspartic acid salt. An analysis revealed that the optical purity of the L-phenylalanine contained in this salt was 98%. The molar ratio of L-phenylalanine to N-carbobenzoxy-L-aspartic acid contained in this salt was 1:1.5. An X-ray diffraction pattern of this salt in powder form had peaks at 2θ=4, 16.2, 17.4, 17.6, 18.6, 19.1, 24.6 and 28.8 (degrees).

후처리

  1. custom) The resulting crystal was separated
  2. washwashed with 10 ml of water
  3. customdried

출처 및 근거

ORD 기록
ord-fc11b455a0314aad9f6b2359a52efcad
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04610827

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