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Acetic Acid → 3-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid

HRID 1061723
ノート
印刷プレビュー

反応式

HRID 1061723 の反応式
C[O:2][C:3](=[O:39])[CH:4]([NH:26][S:27]([C:30]1[C:35]([CH3:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:31]=1[CH3:38])(=[O:29])=[O:28])[CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([C:14](=[O:25])[NH:15][CH2:16][CH2:17][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:12][CH:13]=1)=[O:8].[OH-].[Li+].C(O)(=O)C>C(#N)C.C(OCC)(=O)C>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][CH2:17][CH2:16][NH:15][C:14]([C:11]1[S:10][C:9]([C:7]([NH:6][CH2:5][CH:4]([NH:26][S:27]([C:30]2[C:31]([CH3:38])=[CH:32][C:33]([CH3:37])=[CH:34][C:35]=2[CH3:36])(=[O:29])=[O:28])[C:3]([OH:39])=[O:2])=[O:8])=[CH:13][CH:12]=1)=[O:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 537556273-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester

生成物 1

HCID 698008343-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid収率 86%

試薬・触媒・溶媒 2

HCID 6342
Acetonitrile
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester (40 mg, 0.069 mmol), lithium hydroxide (34 mg, 1.39 mmol), in acetonitrile (10 mL) was stirred for 4 hrs at room temperature. The solvent was removed and the crude reaction product was taken up in ethyl acetate (40 mL). The solution was neutralized with acetic acid (1.0 mL). Solvent was than dried over sodium sulfate and evaporated. Purification of the residue on silica gel (10% MeOH-EtOAc) gave 40 mg of pure acetic acid salt of 3-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid (86%). 1HNMR (300 MHz, CD3OD) δ: 2.22 (s, 3H), 2.61 (s, 6H), 3.57 (m, 4H), 3.82 (m, 2H), 6.50(d, 1H), 6.69(m, 2H), 6.90(s, 2H), 7.42(m, 3H), 8.01 (m, 1H). Compound XXXVI: 2-Benzenesulfonylamino-3-({5-[(1H-benzoimidazol-2-ylmethyl)-carbamoyl]-thiophene-2-carbonyl-amino)-propionic acid.

後処理

  1. customThe solvent was removed
  2. customthe crude reaction product
  3. dry with materialthan dried over sodium sulfate
  4. customevaporated
  5. customPurification of the residue on silica gel (10% MeOH-EtOAc)

出典と根拠

ORDレコード
ord-fe2d2959bdab4aa98d09f673bac84a1c
出典データセット
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06960594B2

反応ノート

読み込み中…

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