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Hydrochloric Acid → HCID 67572402, 화합물

HRID 1292695
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HRID 1292695 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

HCID 67572402HCID 67572402, 화합물

시약·촉매·용매 3

HCID 176Acetic Acid용매
HCID 8857
Ethyl Acetate
용매
2회
HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-12a37a28a77c469789949c7f2aa23c62
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05756528

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