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

HRID 1061722ノート

反応式

HRID 1061722 の反応式
CO[C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH2:12][CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-].N1C=CC=CC=1NCCNC(C1SC(C(O)=O)=CC=1)=O.C(OC(NC[CH2:53][O:54][C:55](=[O:72])[CH:56]([NH:59][S:60]([C:63]1[C:68]([CH3:69])=[CH:67][C:66]([CH3:70])=[CH:65][C:64]=1[CH3:71])(=[O:62])=[O:61])[CH2:57][NH2:58])=O)(C)(C)C.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=N)C>CN(C=O)C>[CH3:53][O:54][C:55](=[O:72])[CH:56]([NH:59][S:60]([C:63]1[C:68]([CH3:69])=[CH:67][C:66]([CH3:70])=[CH:65][C:64]=1[CH3:71])(=[O:62])=[O:61])[CH2:57][NH:58][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH2:12][CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:8][CH:9]=1)=[O:4]

参加物

8

反応物 6

HCID 3939Lithium HydroxideHCID 206776163-Amino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid 2-tert-butoxycarbonylamino-ethyl esterHCID 21883477Ethylcarbodiimide hydrochlorideHCID 233982735-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl esterHCID 542453455-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carboxylic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 537556273-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester収率 87%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester was hydrolyzed with LiOH as described before. To a mixture of 5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carboxylic acid (38 mg, 0.12 mmol), salt of 3-amino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid 2-tert-butoxycarbonylamino-ethyl ester (47 mg, 0.14 mmol), hydroxybenzotriazole (21 mg, 0.15 mmol) in DMF (20 mL), was added 1-(3-dimethylamino) propyl)-3-ethylcarbodiimide hydrochloride (29 mg, 0.15 mmol). The reaction was stirred overnight at room temperature. Insolubles were removed by filtration and the solvent was evaporated. Purification of the residue on silica gel (10% MeOH/EtOAc) gave 60 mg (87%) of pure 3-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester. 1HNMR (300 MHz, CDCl3) δ: 2.22 (s, 3H), 2.61 (s, 6H), 3.55 (m, 4H), 3.82 (m, 1H), 4.09 (m, 1H), 6.50(d, 1H), 6.69(t, 1H), 6.90(s, 2H), 7.05(t, 1H), 7.40(m, 3H), 8.10 (s, 1H), 8.43(m, 1H).

後処理

  1. customInsolubles were removed by filtration
  2. customthe solvent was evaporated
  3. customPurification of the residue on silica gel (10% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-cd1649773cca4f5ab7e4db6d498e54d7
出典データセット
uspto-grants-2005_11
特許番号
US06960594B2

反応ノート

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