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

HRID 1702809노트

반응식

HRID 1702809 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-be04438943f443529b1376add4e4c5c6
출처 데이터셋
uspto-grants-1982_09
특허 번호
US04349552

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