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1,2-Dichloroethane → Methyl 4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-imidazole-2-carboxylate

HRID 1968485
ノート
印刷プレビュー

反応式

HRID 1968485 の反応式
C(OC([NH:8][C:9]1[N:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[N:12]([CH3:14])[CH:13]=1)=O)(C)(C)C.Cl.[C:20]([O:24][C:25]([NH:27][C:28]1[N:29]=[C:30]([C:34]([OH:36])=O)[N:31]([CH3:33])[CH:32]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(Cl)CCl.CCN(C(C)C)C(C)C>C(O)C.C1(C)C=CC=CC=1.CC(N(C)C)=O>[C:20]([O:24][C:25]([NH:27][C:28]1[N:29]=[C:30]([C:34]([NH:8][C:9]2[N:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[N:12]([CH3:14])[CH:13]=2)=[O:36])[N:31]([CH3:33])[CH:32]=1)=[O:26])([CH3:21])([CH3:22])[CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27572264-(((1,1-Dimethylethoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylic acidHCID 11379828METHYL 4-(TERT-BUTOXYCARBONYLAMINO)-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE

生成物 1

HCID 59440227
Methyl 4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-imidazole-2-carboxylate
収率 71.5%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 31374Dimethylacetamide溶媒

実験手順

Methyl 4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxylate (2.50 g, 9.80 mmol) in 30 ml of EtAc was added 6 ml of HCl (conc.). After stirred for 30 min, the mixture was diluted with ethanol and toluene, concentrated and co-evaporated with ethanol/toluene (1:1, 3×50 ml) to dryness compound without further purification. To the dryness compound was added 4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxylic acid (2.36 g, 9.8 mmol), EDC (5.90 g, 30.7 mmol), DIPEA (1.70 ml, 9.8 mmol) and 80 ml of DMA. The mixture was stirred under Ar overnight, concentrated, diluted with THF/EtAc (1:2, 150 ml), and washed 1M NaH2PO4/NaCl (conc) and NaHCO3 (conc) separately. The organic solvent layer was separated and dried over MgSO4, filtered, concentrated and purified on SiO2 chromatography eluted with EtAc/DCM (1:25 to 1:15) to afford 2.65 g (71.5%) of the title product. 1H NMR (DMSO) 11.17 (s, 1H), 10.48 (s, 1H), 7.58 (s, 1H), 7.32 (s, 1H), 4.01 (s, 3H), 3.94 (s, 3H), 3.92 (s, 3H), 1.45 (s, 9H); 13C NMR 160.60, 157.30, 135.92, 135.45, 132.86, 126.12, 114.83, 79.50, 52.70, 35.58, 34.92, 28.08; MS m/z+401.8 (M+Na).

後処理

  1. concentrationconcentrated and co-evaporated with ethanol/toluene (1:1, 3×50 ml) to dryness compound without further purification
  2. stirringThe mixture was stirred under Ar overnight
  3. concentrationconcentrated
  4. additiondiluted with THF/EtAc (1:2, 150 ml)
  5. washwashed 1M NaH2PO4/NaCl (conc) and NaHCO3 (conc) separately
  6. customThe organic solvent layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified on SiO2 chromatography
  11. washeluted with EtAc/DCM (1:25 to 1:15)

出典と根拠

ORDレコード
ord-d7ffbb117c4e492980e862aa45f224d4
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426402B2

反応ノート

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