Triphenylphosphine → HCID 131723880, 화합물

HRID 411778

반응식

HRID 411778 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P([O-])(OCC1C=CC=CC=1)(OCC1C=CC=CC=1)=O.[CH3:39][N:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([C:49]2[C:50](=[O:76])[N:51]([CH2:68][O:69][C:70](=[O:75])[NH:71]CCO)[C:52](=[O:67])[C:53]=2[C:54]2[C:62]3[C:57](=[CH:58][C:59]([N+:63]([O-:65])=[O:64])=[CH:60][CH:61]=3)[N:56]([CH3:66])[CH:55]=2)=[CH:41]1>C1COCC1>[CH3:39][N:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([C:49]2[C:50](=[O:76])[N:51]([CH2:68][O:69][C:70](=[O:75])[NH2:71])[C:52](=[O:67])[C:53]=2[C:54]2[C:62]3[C:57](=[CH:58][C:59]([N+:63]([O-:65])=[O:64])=[CH:60][CH:61]=3)[N:56]([CH3:66])[CH:55]=2)=[CH:41]1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 4193600DibenzylphosphateHCID 9892774(2-hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester

생성물 1

HCID 131723880HCID 131723880, 화합물수율 54%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

Triphenylphosphine (95 mg, 0.36 mmol) and dibenzyl phosphate (101 mg, 0.36 mmol) were added to a solution of (2-Hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester, prepared as in example 19 (150 mg, 0.289 mmol) in THF (6 mL). The mixture was cooled at −78° C. Diethyl azodicarboxiate (0.057 mL, 0.36 mmol) was added dropwise over 5 min. The cooling bath was removed and the mixture was stirred overnight. The mixture was then evaporated. Chromatography of the residue over silica gel using 2:1-4:1 EtOAc/hexanes gave [2-bis-benzyloxy-phosphoryloxy)-ethyl]-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester (121 mg, 54%).

후처리

  1. additionDiethyl azodicarboxiate (0.057 mL, 0.36 mmol) was added dropwise over 5 min
  2. customThe cooling bath was removed
  3. customThe mixture was then evaporated

출처 및 근거

ORD 기록
ord-5920eaef75b444e2995e032250df7c23
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559164B1

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