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Sulfuric Acid → 3(S)-(6-Methoxy-pyridin-3-yl)-3-{2-oxo-3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propyl]-2,3-dihydro-imidazol-1-yl}-propionic acid tert-butyl ester

HRID 993246
ノート
印刷プレビュー

反応式

HRID 993246 の反応式
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[C:13]([O:17][C:18](=[O:36])[CH2:19][C@H:20]([NH:29][CH2:30][CH:31](OC)OC)[C:21]1[CH:22]=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C.[N:44]1[C:49]2[NH:50][CH2:51][CH2:52][CH2:53][CH2:54][C:48]=2[CH:47]=[CH:46][C:45]=1[CH2:55][CH2:56][CH2:57][NH2:58].OS(O)(=O)=O>C1COCC1>[C:13]([O:17][C:18](=[O:36])[CH2:19][C@@H:20]([C:21]1[CH:22]=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[N:29]1[CH:30]=[CH:31][N:58]([CH2:57][CH2:56][CH2:55][C:45]2[CH:46]=[CH:47][C:48]3[CH2:54][CH2:53][CH2:52][CH2:51][NH:50][C:49]=3[N:44]=2)[C:5]1=[O:11])([CH3:14])([CH3:15])[CH3:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 1118Sulfuric AcidHCID 8471Triethylamine2 回HCID 94429TriphosgeneHCID 111751973(S)-(2,2-dimethoxyethylamino)-3-(6-methoxypyridin-3-yl)propionate tert butyl esterHCID 184089753-(6,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propylamine

生成物 1

HCID 70127621
3(S)-(6-Methoxy-pyridin-3-yl)-3-{2-oxo-3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propyl]-2,3-dihydro-imidazol-1-yl}-propionic acid tert-butyl ester
収率 208.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of triphosgene (0.246 g, 0.804 mmol) in THF (5 mL) at 0° C. was added a mixture of 1-6 (0.78 g, 2.29 mmol), triethylamine (0.36 mL, 3.09 mmol) and THF (1 mL) over 10 minutes. After 30 minutes, the reaction was allowed to warm to ambient temperature and stir for 1 hour. The mixture was then purged with argon for 30 minutes, and to it was added a mixture of 3-6 (0.435 g, 2.52 mmol), triethylamine (0.36 mL, 3.09 mmol) and THF (5 mL). The mixture was then heated at 0° C. for 2 hours, allowed to cool to ambient temperature. 2M H2SO4 (2.5 mL) was then added, and the mixture stirred for 15 hours. The reaction was then quenched with a 10% w/v solution of K2CO3 (10 mL), diluted with ethyl acetate, washed with water and brine, dried over MgSO4, and concentrated to give 850 mg of 3-7 as a yellow oil, used crude in the next step.

後処理

  1. customThe mixture was then purged with argon for 30 minutes
  2. additionto it was added
  3. temperatureThe mixture was then heated at 0° C. for 2 hours
  4. temperatureto cool to ambient temperature
  5. stirringthe mixture stirred for 15 hours
  6. customThe reaction was then quenched with a 10% w/v solution of K2CO3 (10 mL)
  7. additiondiluted with ethyl acetate
  8. washwashed with water and brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-c565db741aff48ca86873d906c943edd
出典データセット
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06472403B2

反応ノート

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