Sodium cyanoborohydride → HCID 135577948、化合物

HRID 2165721ノート

反応式

HRID 2165721 の反応式
[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]

参加物

5

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 12469743dimethyl N-(4-aminobenzoyl)-L-glutamateHCID 135577947HCID 135577947、化合物

生成物 1

HCID 135577948HCID 135577948、化合物収率 49%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8d5214c7d00a4bfc9dcd2383595b1050
出典データセット
uspto-grants-1990_07
特許番号
US04940713

反応ノート

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