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

HRID 1061723Notes

Reaction equation

HRID 1061723 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fe2d2959bdab4aa98d09f673bac84a1c
Source dataset
uspto-grants-2005_11
Patent number
US06960594B2

Reaction notes

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