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Hydrochloric Acid → HCID 67572402、化合物

HRID 1292695
ノート
印刷プレビュー

反応式

HRID 1292695 の反応式
C(O[C:6]([NH:8][C@@H:9]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:10][N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[CH3:22])C(=O)C)=O)(C)(C)C.Cl.[C:28]([C:30]1[CH:43]=[CH:42][C:33]([CH2:34][N:35]2[C:39](C=O)=[CH:38][N:37]=[CH:36]2)=[CH:32][CH:31]=1)#[N:29].C([BH3-])#N.[Na+]>CCOC(C)=O.CO.C1COCC1.C(O)(=O)C>[C:28]([C:30]1[CH:31]=[CH:32][C:33]([CH2:34][N:35]2[C:39]([CH2:6][NH:8][C@@H:9]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:10][NH:11][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=3[CH3:22])=[CH:38][N:37]=[CH:36]2)=[CH:42][CH:43]=1)#[N:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrileHCID 18660148HCID 18660148、化合物

生成物 1

HCID 67572402HCID 67572402、化合物

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒
HCID 8857
Ethyl Acetate
溶媒
2 回
HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

Through a solution of the product from Step I (533 mg, 1.47 mmol) in 20 mL of EtOAc at 0° C. was bubbled HCl gas. The saturated solution was warmed to room temperature and stirred for 40 minutes, then concentrated in vacuo. To a solution of this amine salt in 6 mL of 1:1 MeOH/THF at 0° C. was added the aldehyde from Step E (325 mg, 1.54 mmol) and 0.05 mL of acetic acid. After one hour, sodium cyanoborohydride was added (97 mg, 1.54 mmol), and the solution was allowed to warm to room temperature overnight. After ~16 hours, the reaction was poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2 SO4), filtered, and concentrated in vacuo. The resulting product was purified by silica gel chromatography (1-2% MeOH/CHCl3). A portion of this was taken up in EtOAc/Et2O and treated with excess HCl gas, then stripped to provide the titled compound.

後処理

  1. concentrationconcentrated in vacuo
  2. waitAfter one hour
  3. temperatureto warm to room temperature overnight
  4. waitAfter ~16 hours
  5. washwashed with sat. aq. NaHCO3 and brine
  6. customdried (Na2 SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting product was purified by silica gel chromatography (1-2% MeOH/CHCl3)
  10. additiontreated with excess HCl gas

出典と根拠

ORDレコード
ord-12a37a28a77c469789949c7f2aa23c62
出典データセット
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05756528

反応ノート

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