Acetic Acid → 4-(N-((2,4-diamino-6-pteridinyl)methyl)amino)benzoic acid

HRID 1154690

반응식

HRID 1154690 반응식
[CH:1]1[C:6](C(N[C@H](C(O)=O)CCC(O)=O)=O)=[CH:5][CH:4]=[C:3]([NH:19][CH2:20][C:21]2[CH:22]=[N:23][C:24]3[N:30]=[C:29]([NH2:31])[N:28]=[C:27]([NH2:32])[C:25]=3[N:26]=2)[CH:2]=1.[OH-].[Na+].C[C:36]([OH:38])=[O:37]>CC([O-])=O.[Na+].[Cl-].[Cl-].[Zn+2]>[CH:5]1[C:6]([C:36]([OH:38])=[O:37])=[CH:1][CH:2]=[C:3]([NH:19][CH2:20][C:21]2[N:26]=[C:25]3[C:27]([NH2:32])=[N:28][C:29]([NH2:31])=[N:30][C:24]3=[N:23][CH:22]=2)[CH:4]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 169371Aminopterin

생성물 1

HCID 1697484-(N-((2,4-diamino-6-pteridinyl)methyl)amino)benzoic acid수율 86%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 517045Sodium Acetate용매

반응 조건

온도
5 °C

실험 절차

Aminopterin (2.4 g, 0.005 mol) is suspended in 1M NaOAc (500 ml) containing ZnCl2 (0.1 g), and 2N NaOH is added dropwise with stirring until a clear solution forms. Glacial AcOH is then added dropwise to bring the pH to 7.5, and 5 μl of carboxypeptidase G1 (4000 units/ml) is added. The mixture is shaken at 37° C. for 1 day, cooled to 5° C., and suction filtered. The solid is washed thoroughly with H2O, and dried in vacuo on a freeze-drying apparatus to obtain 4-amino-4-deoxypteroic acid (APA) (1.43 g, 86%) as an orange-yellow solid. The analytical sample is prepared by passing a small amount of this material through a microcrystalline cellulose column, with 0.1M glycine, pH 10, as the eluent. Appropriate fractions are pooled and acidified with AcOH, and the precipitate is collected, washed with H2O, and dried in vacuo over P2O5 ; Rf 0.1 (cellulose, pH 7.4 phosphate), dark absorbing spot; UVλmax (0.1N HCl) 243 nm (ε 18,500), 297 (23,900), 337 infl (13,700); UVλmax (0.1N NaOH) 261 nm (ε 30,400), 371 (9,100). Analysis for C, H, and N confirms the composition of APA.

후처리

  1. additionis added dropwise
  2. addition(4000 units/ml) is added
  3. stirringThe mixture is shaken at 37° C. for 1 day
  4. filtrationsuction filtered
  5. washThe solid is washed thoroughly with H2O
  6. customdried in vacuo on a freeze-drying apparatus

출처 및 근거

ORD 기록
ord-26775886c76d4b87810420f33ba47ed3
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04490529

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