Triethylamine → HCID 15132640, 화합물

HRID 467151

반응식

HRID 467151 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])(C)C.[CH2:16](P(C#N)(CC)=O)C.C([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])C.[CH:31]1C=[CH:35][CH:34]=[CH:33][CH:32]=1.[C:37]([O:40][CH2:41]C)(=[O:39])C>CN(C)C=O>[CH3:16][O:39][CH:37]([O:40][CH3:41])[C@@H:29]1[CH2:30][CH2:28][CH2:27][N:26]1[C:10](=[O:12])[C@H:9]1[CH2:13][CH2:14][CH2:15][N:8]1[C:6]([O:5][CH2:1][C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:7]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 13586794DiethylphosphorylcyanideHCID 21583983Benzene ethyl acetate

생성물 1

HCID 15132640HCID 15132640, 화합물수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

L-prolinal dimethyl acetal hydrochloride obtained in the same manner as in Example 1 is dissolved in dimethylformamide (4 ml) containing tert-butoxycarbonyl-D-proline (790 mg, 3.17 mmol) and diethylphosphoryl cyanide (0.48 ml, 3.16 mmol). To the solution is added dropwise triethylamine (1.15 ml, 8.25 mmol) under cooling and agitation in an ice-methanol bath. The mixture is continued to be stirred for one hour under cooling and then for one hour at room temperature. Benzene-ethyl acetate (2:1, 150 ml) is added to the reaction mixture, and the organic layer is separated, washed successively with a saturated aqueous solution of sodium hydrogen carbonate (15 ml), water (15 ml) and a saturated aqueous solution of edible salt (15 ml), dried over sodium sulfate and filtered. The filtrate is concentrated to dryness under reduced pressure. The residue is purified by column chromatography on silica gel (benzene-ethyl acetate, 1:2→1:1) to give 713 mg (63%) of the title compound as a pale yellow syrup.

후처리

  1. temperatureunder cooling
  2. temperatureunder cooling
  3. waitfor one hour at room temperature
  4. customthe organic layer is separated
  5. washwashed successively with a saturated aqueous solution of sodium hydrogen carbonate (15 ml), water (15 ml)
  6. dry with materiala saturated aqueous solution of edible salt (15 ml), dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated to dryness under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel (benzene-ethyl acetate, 1:2→1:1)

출처 및 근거

ORD 기록
ord-fa19b9577d11491c9393047d151120d8
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05158970

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