Sodium cyanoborohydride → HCID 135577948, 화합물

HRID 2165721노트

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HRID 2165721 반응식
[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:21])[C:8]([CH2:18][CH:19]=O)=[C:9]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[N:10]=1)(=[O:3])[CH3:2].[NH2:22][C:23]1[CH:42]=[CH:41][C:26]([C:27]([NH:29][C@H:30]([C:37]([O:39][CH3:40])=[O:38])[CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:28])=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:21])[C:8]([CH2:18][CH2:19][NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([NH:29][C@H:30]([C:37]([O:39][CH3:40])=[O:38])[CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:28])=[CH:41][CH:42]=2)=[C:9]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[N:10]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 12469743dimethyl N-(4-aminobenzoyl)-L-glutamateHCID 135577947HCID 135577947, 화합물

생성물 1

HCID 135577948HCID 135577948, 화합물수율 49%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of 2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)acetaldehyde (1.74 g, 5.92 mmol) and dimethyl N-(4-aminobenzoyl)-L-glutamate (J. Am. Chem. Soc., 1958, 80, 5779) (1.74 g, 5.92 mmol) in acetic acid (90 ml) was stirred for 10 minutes. Sodium cyanoborohydride (0.84 g, 13.4 mmol) was added in small portions over 1 hour. After an additional 30 minutes, the reaction was spin evaporated in vacuo to a thick oil. The oil was dissolved in ethyl acetate (500 ml) and washed with 5% aqueous sodium bicarbonate until neutral, water (50 ml), brine (50 ml), dried with magnesium sulfate and spin evaporated in vacuo. Recrystallization from ethyl acetate, with filtration to remove insolubles, yielded 1.5 g (49% of theory) of dimethyl N-[4-[2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)ethylamino]benzoyl]-L-glutamate, mp 168°-178° C. Recrystallization from ethyl acetate (Norite) gave 0.830 g (25% of theory) of the analytical sample, mp 176°-179° C.

후처리

  1. customevaporated in vacuo to a thick oil
  2. dissolutionThe oil was dissolved in ethyl acetate (500 ml)
  3. washwashed with 5% aqueous sodium bicarbonate until neutral, water (50 ml), brine (50 ml)
  4. dry with materialdried with magnesium sulfate
  5. customspin evaporated in vacuo
  6. customRecrystallization from ethyl acetate
  7. filtrationwith filtration
  8. customto remove insolubles

출처 및 근거

ORD 기록
ord-8d5214c7d00a4bfc9dcd2383595b1050
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04940713

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