Acetic Acid → tert-Butyl {2-[(5-carbamoyl-1H-imidazol-4-yl)amino]ethyl}carbamate

HRID 912719노트

반응식

HRID 912719 반응식
Cl.[NH2:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]([NH2:10])=[O:9].C(N(CC)CC)C.C(O)(=O)C.[C:22]([NH:29][CH2:30][CH:31]=O)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO>[C:8]([C:4]1[NH:5][CH:6]=[N:7][C:3]=1[NH:2][CH2:31][CH2:30][NH:29][C:22](=[O:23])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:9])[NH2:10]

참가 물질

8

반응물 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5003444Sodium cyanoborohydrideHCID 178479549HCID 178479549, 화합물

생성물 1

HCID 86631143tert-Butyl {2-[(5-carbamoyl-1H-imidazol-4-yl)amino]ethyl}carbamate수율 55.1%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

The reaction mixture of 5-amino-imidazole-4-carboxamide hydrochloride (10 g, 62 mmol) and triethylamine (8.7 mL, 63 mmol) in anhydrous methanol (100 mL) was stirred for 15 min. Acetic acid (0.9 mL, 16 mmol) and N-boc-2-aminoacetaldehyde (11 g, 67 mmol) were added. The reaction mixture was stirred for 3 h, then sodium cyanoborohydride (5 g, 80 mmol) was added and the mixture was stirred o.n. A solution of saturated sodium bicarbonate was added and most of the methanol was removed in vacuo. The mixture was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated. Purification by silica gel column chromatography, (dichloromethane/ammonia (7N in methanol), 0-6%) gave 9.2 g (55% yield) of the title compound.

후처리

  1. stirringThe reaction mixture was stirred for 3 h
  2. stirringthe mixture was stirred o.n
  3. customwas removed in vacuo
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customPurification by silica gel column chromatography, (dichloromethane/ammonia (7N in methanol), 0-6%)

출처 및 근거

ORD 기록
ord-d10587cb67d94995b38a212b3516c023
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026244B2

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