Triethylamine → 3-[[(1,1-Dimethylethoxy)carbonyl]amino]bicyclo[2.2.1]heptane-2-carboxylic acid

HRID 1702809ノート

反応式

HRID 1702809 の反応式
[NH2:1][CH:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[C:9]([OH:11])=[O:10].C(N(CC)CC)C.[C:19]([O:23][C:24](ON=C(C1C=CC=CC=1)C#N)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O.O1CCOCC1>[C:19]([O:23][C:24]([NH:1][CH:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[C:9]([OH:11])=[O:10])=[O:25])([CH3:22])([CH3:21])[CH3:20]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 5508363-Aminobicyclo[2.2.1]heptane-2-carboxylic acid

生成物 1

HCID 170393413-[[(1,1-Dimethylethoxy)carbonyl]amino]bicyclo[2.2.1]heptane-2-carboxylic acid収率 62.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 3-aminonorbornane-2-carboxylic acid (12.6 g.) in a mixture of water (100 ml.) and dioxane (100 ml.) were added triethylamine (12.2 g.) and 2-tert-butoxycarbonyloxyimino-2-phenylacetonitrile (16.2 g.). The mixture was stirred for 5 hours at ambient temperature and washed with ethyl acetate at pH 10 (each 250 ml., 2 times). The aqueous layer was adjusted to pH 2 with 10% aqueous hydrochloric acid. The acidified solution was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure. The residue was pulverized with isopropyl ether to give 3-(N-tert-butoxycarbonylamino)norbornane-2-carboxylic acid (10.5 g.).

後処理

  1. washwashed with ethyl acetate at pH 10 (each 250 ml
  2. extractionThe acidified solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-be04438943f443529b1376add4e4c5c6
出典データセット
uspto-grants-1982_09
特許番号
US04349552

反応ノート

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