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

HRID 1061722노트

반응식

HRID 1061722 반응식
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]

참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-cd1649773cca4f5ab7e4db6d498e54d7
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960594B2

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