Imidazol-1-YL-oxo-acetic acid tert-butyl ester → 2-Amino-7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester

HRID 2188003노트

반응식

HRID 2188003 반응식
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][N:18]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4OCC4C=CC=CC=4)[C:19]3=[O:36])[N:13]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:44])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:45]([O:49][C:50]([C:52]1[C:60]2[CH2:59][CH2:58][N:57]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[CH:56]([CH2:68][N:69]3[C:77](=[O:78])[C:76]4[C:71](=[CH:72][CH:73]=[CH:74][C:75]=4OCC4C=CC=CC=4)[C:70]3=[O:87])[C:55]=2[S:54][C:53]=1[NH2:88])=[O:51])([CH3:48])([CH3:47])[CH3:46].C(OC(=O)C(N1C=CN=C1)=O)(C)(C)C>ClCCl>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][N:18]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:36])[N:13]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:44])=[O:7])([CH3:3])([CH3:4])[CH3:2].[C:45]([O:49][C:50]([C:52]1[C:60]2[CH2:59][CH2:58][N:57]([C:61]([O:63][C:64]([CH3:66])([CH3:67])[CH3:65])=[O:62])[CH:56]([CH2:68][N:69]3[C:70](=[O:87])[C:71]4[C:76](=[CH:75][CH:74]=[CH:73][CH:72]=4)[C:77]3=[O:78])[C:55]=2[S:54][C:53]=1[NH2:88])=[O:51])([CH3:46])([CH3:47])[CH3:48]

참가 물질

6

반응물 3

HCID 11217804Imidazol-1-YL-oxo-acetic acid tert-butyl esterHCID 695856252-Amino-7-(4-benzyloxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl esterHCID 695860022-Amino-5-(4-benzyloxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester

생성물 2

HCID 695856542-Amino-7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl esterHCID 695857032-Amino-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the above mixture of 2-amino-5-(4-benzyloxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester and 2-amino-7-(4-benzyloxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (0.15 g, 0.24 mmol) in distilled dichloromethane (4 ml) under nitrogen was added imidazol-1-yl-oxo-acetic acid tert-butyl ester (0.14 g, 0.72 mmol) and the reaction mixture was stirred at ambient temperature for 1.5 hour. The volatiles were evaporated in vacuo and the crude residue was purified by silica gel chromatography using dichloromethane as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 50 mg of 2-(tert-butoxyoxalyl-amino)-5-(4-benzyloxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (A) and 50 mg of 2-(tert-butoxyoxalyl-amino)-7-(4-benzyloxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (B). Another 50 mg remained as a mixture of the two isomers (A) and (B).

후처리

  1. customThe volatiles were evaporated in vacuo
  2. customthe crude residue was purified by silica gel chromatography
  3. customPure fractions were collected
  4. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-2dd88ac91ed147da8143034f4623cf8a
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06410556B1

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