Triphenylphosphine → Ethyl 2-[4-[((2S)-1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate

HRID 1901338

반응식

HRID 1901338 반응식
N(C(OCC)=O)=NC(OCC)=O.[C:13]([C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21]([CH2:23][CH:24]([C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=3)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][C:19]=2[CH:37]=1)#[N:14].[C:38]([O:42][C:43]([N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[CH2:50]O)=[O:44])([CH3:41])([CH3:40])[CH3:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:38]([O:42][C:43]([N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[CH2:50][O:36][C:33]1[CH:32]=[CH:31][C:30]([CH:24]([CH2:23][C:21]2[O:22][C:18]3[CH:17]=[CH:16][C:15]([C:13]#[N:14])=[CH:37][C:19]=3[CH:20]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:35][CH:34]=1)=[O:44])([CH3:41])([CH3:39])[CH3:40]

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 643448(S)-(-)-N-Boc-prolinol2회HCID 21844506Ethyl 3-(5-cyano-2-benzofuranyl)-2-(4-hydroxyphenyl)propionate

생성물 1

HCID 57286602Ethyl 2-[4-[((2S)-1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate수율 51.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1.04 g of diethyl azodicarboxylate was added to 300 ml of a tetrahydrofuran solution containing 1 g of ethyl 3-(5-cyano-2-benzofuranyl)-2-(4-hydroxyphenyl)propionate, 1.2 g of (2S)-1-tert-butoxycarbonyl-2-pyrrolidinemethanol and 1.56 g of triphenylphosphine, and the thus prepared mixture was stirred at room temperature for 18 hours. To the resulting reaction solution were added 0.6 g of (2S)-1-tert-butoxycarbonyl-2-pyrrolidinemethanol, 0.78 g of triphenylphosphine and 0.52 g of diethyl azodicarboxylate, followed by additional stirring at room temperature for 18 hours. Thereafter, the reaction solution thus obtained was concentrated to dryness, and the resulting residue was purified by subjecting it to silica gel column chromatography using a toluene/ethyl acetate mixture as an eluant. In this way, 790 mg of the title compound was obtained in the form of colorless oil.

후처리

  1. customTo the resulting reaction solution
  2. stirringby additional stirring at room temperature for 18 hours
  3. customThereafter, the reaction solution thus obtained
  4. concentrationwas concentrated to dryness
  5. customthe resulting residue was purified

출처 및 근거

ORD 기록
ord-9f81d53f06e04d7abb8b50afe1573dad
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576343

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