2-(6-(Bis(carboxymethyl)amino)-5-(2-(2-(bis(carboxymethyl)amino)-5-methylphenoxy)ethoxy)-2-benzofuranyl)-5-oxazolecarboxylic acid → Bapta

HRID 2400176

반응식

HRID 2400176 반응식
C[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10]([OH:12])=[O:11])=[C:4]([O:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[C:25]3C=C(C4OC(C(O)=O)=CN=4)O[C:24]3=[CH:23][C:22]=2[N:38]([CH2:43][C:44]([OH:46])=[O:45])[CH2:39][C:40]([OH:42])=[O:41])[CH:3]=1.[H][H]>C(O)(=O)C.[Pd]>[CH:7]1[CH:2]=[CH:3][C:4]([O:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:38]([CH2:43][C:44]([OH:46])=[O:45])[CH2:39][C:40]([OH:42])=[O:41])=[C:5]([N:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10]([OH:12])=[O:11])[CH:6]=1

참가 물질

5

반응물 2

HCID 570542-(6-(Bis(carboxymethyl)amino)-5-(2-(2-(bis(carboxymethyl)amino)-5-methylphenoxy)ethoxy)-2-benzofuranyl)-5-oxazolecarboxylic acidHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 104751Bapta

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

Synthesis of a BAPTA tetramethyl ester that contains a phenolic reactive group (Compound XXV). A hydroxy derivative of BAPTA (4-hydroxy-BAPTA) is synthesized by hydrogenation of one of the key intermediate in the synthesis of the Ca2+ indicator fura-2 [U.S. Pat. No. 4,603,209]. For instance 9.8 g of 4-benzyloxy-5'-methyl BAPTA tetramethyl ester is hydrogenated in 50 mL glacial acetic acid in the presence of 0.3 g 10% palladium on charcoal at 40 psi hydrogen pressure for four hours. The reaction is filtered through a pad of Celite to remove the catalyst and the yellow filtrate is evaporated under reduced pressure to give a light brown oil. This is triturated with 50 mL methanol to yield 7.2 g of 4-hydroxy BAPTA tetramethyl ester as a colorless solid (Compound XXV).

후처리

  1. filtrationThe reaction is filtered through a pad of Celite
  2. customto remove the catalyst
  3. customthe yellow filtrate is evaporated under reduced pressure
  4. customto give a light brown oil
  5. customThis is triturated with 50 mL methanol

출처 및 근거

ORD 기록
ord-ad0318f94f434a79ba125c3e38442a97
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05453517

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