Diisopropylethylamine → 2-({4-[(2-Chloro-4-nitrophenyl)diazenyl]phenyl}ethylamino)ethyl (2S,4R)-2-{[bis(4-Methoxyphenyl)phenylmethoxy]methyl}-4-{[bis(methylethyl)amino](2-cyanoethoxy)phosphinooxy}pyrrolidinecarboxylate

HRID 47961

반응식

HRID 47961 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[O:10][CH2:11][C@H:12]2[N:16]([C:17]([O:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N:31]=[N:32][C:33]4[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=4[Cl:42])=[CH:27][CH:26]=3)=[O:18])[CH2:15][C@H:14]([OH:43])[CH2:13]2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[CH:67]([N:70]([CH:78]([CH3:80])[CH3:79])[P:71](Cl)[O:72][CH2:73][CH2:74][C:75]#[N:76])([CH3:69])[CH3:68].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:50]2[CH:51]=[CH:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[O:10][CH2:11][C@@H:12]2[CH2:13][C@@H:14]([O:43][P:71]([N:70]([CH:78]([CH3:80])[CH3:79])[CH:67]([CH3:68])[CH3:69])[O:72][CH2:73][CH2:74][C:75]#[N:76])[CH2:15][N:16]2[C:17]([O:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([N:31]=[N:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=3[Cl:42])=[CH:29][CH:30]=2)=[O:18])=[CH:5][CH:4]=1

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27348442-Cyanoethyl N,N-diisopropylchlorophosphoramiditeHCID 865847172-({4-[(2-Chloro-4-nitrophenyl)diazenyl]phenyl}ethylamino)ethyl (5S,3R)-5-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}-3-hydroxypyrrolidinecarboxylate

생성물 1

HCID 865847192-({4-[(2-Chloro-4-nitrophenyl)diazenyl]phenyl}ethylamino)ethyl (2S,4R)-2-{[bis(4-Methoxyphenyl)phenylmethoxy]methyl}-4-{[bis(methylethyl)amino](2-cyanoethoxy)phosphinooxy}pyrrolidinecarboxylate수율 93%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4 (12.63 g, 15.91 mmol) dissolved in 440 ml of anhydrous methylene chloride, containing 8.0 ml of N,N-diisopropylethylamine, was added 5.94 ml of 2-cyanoethyl diisopropylchlorophosphoramidite. The solution was stirred 30 min under argon at room temperature. The reaction mixture was treated with 10 ml of methanol and poured into 400 ml of 5% sodium bicarbonate solution. The organic phase was dried over sodium sulfate and evaporated. The residue was purified by silica gel chromatography eluting with a gradient of 40-20% hexane in ethyl acetate (2% triethylamine). The pure product fractions were evaporated affording an amorphous solid: 14.75 g (93% yield). 31P NMR (DMSO-d6) δ146.93 (singlet). Anal. Calcd for C52H61ClN7O9*1.0 H2O: C, 61.68; H, 6.27; N, 9.68. Found: C, 61.44; H, 6.47; N, 9.35.

후처리

  1. dry with materialThe organic phase was dried over sodium sulfate
  2. customevaporated
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with a gradient of 40-20% hexane in ethyl acetate (2% triethylamine)
  5. customThe pure product fractions were evaporated
  6. customaffording an amorphous solid

출처 및 근거

ORD 기록
ord-334681c886214bcca049d22de52b2c19
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699975B2

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