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Triethylamine → trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester

HRID 2107492
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HRID 2107492 반응식
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:13]2[C:14]([OH:16])=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Cl)=[CH:34][CH:33]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][O:15][C:14](=[O:16])[C@@H:13]2[CH2:17][C@@H:18]([OH:20])[CH2:19][N:12]2[C:10]([O:9][CH2:8][C:7]2[CH:21]=[CH:22][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])=[CH:34][CH:33]=1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 10566895trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

생성물 1

HCID 13504318trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

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온도
70 °C

실험 절차

15.0 g of trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline and 13.5 ml of triethylamine were dissolved in 150 ml of dried dimethylformamide, and 12.66 ml of p-methoxybenzyl chloride was added dropwise to the solution under a nitrogen stream, followed by stirring at 70° C. for 10 hours. The reaction mixture was diluted with 500 ml of ethyl acetate, washed with water, dried over sodium sulfate and distilled off to remove the solvent. Recrystallization of the residue from diethyl ether gave trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester.

후처리

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. distillationdistilled off
  4. customto remove the solvent
  5. customRecrystallization of the residue from diethyl ether

출처 및 근거

ORD 기록
ord-e01e5681e4cb4f9c90236c6cbda4fe9b
출처 데이터셋
uspto-grants-1990_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04933333

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