Succinic anhydride → HCID 86633362、化合物

HRID 1926460

反応式

HRID 1926460 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:7][CH:6]=[CH:5]2.CN1CCOCC1.[C:23]1(=[O:29])[O:28][C:26](=[O:27])[CH2:25][CH2:24]1>CN(C=O)C>[S:12]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([NH:1][C:23](=[O:29])[CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:3]2)([OH:15])(=[O:13])=[O:14]

参加物

5

反応物 3

HCID 7922Succinic anhydrideHCID 79724-MethylmorpholineHCID 664706-Aminonaphthalene-1-sulphonic acid

生成物 1

HCID 86633362HCID 86633362、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

6-Amino-1-naphtalenesulfonic acid (Dahl's acid) (1 eq, 0.5 mmol,) was dissolved in DMF containing N-methylmorpholine (NMM) (2 eq), and succinic anhydride (10 eq) was then added. After over night reaction the solvent was removed under reduced pressure and the product was purified by preparative RP-HPLC (Reversed Phase HPLC). The column (Phenomenex Luna C18 10μ, 22×250 mm) was eluted at 10 ml/min with a gradient of 5 to 15% acetonitrile (ACN) in 0.1% aq TFA over 40 min. The desired peak fractions collected from six consecutive runs were pooled and lyophilized affording 146 mg of pure N-(−5-Sulfo-naphthalen-2-yl)-succinamic acid 2. Analytical RP-HPLC: tR=16.7 min, (Phenomenex Luna 5μ, 4.6×250 mm, 5-15% ACN in 0.1% aq TFA over 20 min at 1 ml/min, λ=214 nm). Electrospray MS: [M+H]+ of product expected at 324.0 m/z, found at 324.0 m/z.

後処理

  1. additionwas then added
  2. customAfter over night reaction the solvent
  3. customwas removed under reduced pressure
  4. customthe product was purified by preparative RP-HPLC (Reversed Phase HPLC)
  5. washThe column (Phenomenex Luna C18 10μ, 22×250 mm) was eluted at 10 ml/min with a gradient of 5 to 15% acetonitrile (ACN) in 0.1% aq TFA over 40 min
  6. customThe desired peak fractions collected from six consecutive runs

出典と根拠

ORDレコード
ord-65fbd32d274a4501974729616691675c
出典データセット
uspto-grants-2012_05
特許番号
US08182790B2

関連ノート

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