Triethylamine → (3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dione

HRID 2413398노트

반응식

HRID 2413398 반응식
ClC(OCC)=O.[CH2:7]([N:14]1[C@H:18]([C:19](OC)=[O:20])[C@H:17]([C:23](O)=[O:24])[N:16]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:15]1=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>O1CCCC1>[CH2:26]([N:16]1[C@H:17]2[CH2:23][O:24][C:19](=[O:20])[C@H:18]2[N:14]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:15]1=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 11428617(4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid

생성물 1

HCID 119819(3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dione수율 64.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of ethyl chloroformate (0.54 g) in tetrahydrofuran (2 ml) was added dropwise to a mixture of (4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (mp., 149°-150° C., [α]36525 =-27.4° at c=1 in DMF, 1.84 g), triethylamine (0.51 g) and tetrahydrofuran (10 ml) at -5° C. The mixture was stirred at the same temperature for 30 minutes. Precipitated triethylamine hydrochloride was filtered off and the filtrate was added dropwise to a solution of sodium borohydride (0.24 g) in 90 % aqueous tetrahydrofuran (10 ml) at -15° C. After reacting, the mixture was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The extract was concentrated under reduced pressure and the residue was purified by chromatography on silica gel column to give (3aS,6aR)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione (1.04 g). M.P., 114°-117° C. [α]D20 =+59.0° (c=1, CHCl3).

후처리

  1. filtrationPrecipitated triethylamine hydrochloride was filtered off
  2. additionthe filtrate was added dropwise to a solution of sodium borohydride (0.24 g) in 90 % aqueous tetrahydrofuran (10 ml) at -15° C
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated under reduced pressure
  5. customthe residue was purified by chromatography on silica gel column

출처 및 근거

ORD 기록
ord-1bdb33f3dec54cca964ccc5c8552c0bc
출처 데이터셋
uspto-grants-1985_01
특허 번호
US04496739

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