Triphenylphosphine → N-carbobenzyloxy-4-(cis)-(4-cyanophenoxy)-L-proline methyl ester

HRID 1769277

반응식

HRID 1769277 반응식
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]([C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)#[N:41].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@H:7]([O:9][C:45]2[CH:46]=[CH:47][C:42]([C:40]#[N:41])=[CH:43][CH:44]=2)[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylateHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 18654599N-carbobenzyloxy-4-(cis)-(4-cyanophenoxy)-L-proline methyl ester수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of N-carbobenzyloxy-trans-4-hydroxy-L-proline methyl ester (10.0 g, 35.8 mmol) in 200 mL of anhydrous THF under N2 was added triphenylphosphine (10.6 g, 39.4 mmol) and 4-cyanophenol (4.7 g, 39.4 mmol). This solution was cooled to 0° C. and then treated with diethylazodicarboxylate (6.3 mL, 39.4 mmol), added dropwise over 30 minutes. The reaction was warmed to room temperature and stirred for 2 days. The solvent was removed in vacuo, and the residue chromatographed (SiO2, 30% ethyl acetate/hexanes) to provide 12.1 g (89%) of N-carbobenzyloxy-4-(cis)-(4-cyanophenoxy)-L-proline methyl ester as a colorless oil. (MS).

후처리

  1. additionadded dropwise over 30 minutes
  2. temperatureThe reaction was warmed to room temperature
  3. customThe solvent was removed in vacuo
  4. customthe residue chromatographed (SiO2, 30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-ac690719893f46f19430c33aa10f4bd1
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380866

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