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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
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HRID 1061723 반응식
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]
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6342
Acetonitrile
용매
HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fe2d2959bdab4aa98d09f673bac84a1c
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06960594B2

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