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

HRID 1088250
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HRID 1088250 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

Trans-1-(p-Nitrobenzyloxycarbonyl)-4-hydroxy-L-proline (15.0 g) and triethylamine (13.5 ml) were dissolved in 150 ml of dry dimethylformamide, and 12.66 ml of p-methoxybenzyl chloride was dropwise added thereto under 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 anhydrous sodium sulfate and distilled to remove the solvent. Recrystallization of the residue from diethyl ether gave trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester. M.P., 83°-85° C.

후처리

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

출처 및 근거

ORD 기록
ord-e406930c75c6477e9cbbd663250c77d7
출처 데이터셋
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04962103

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