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

HRID 53973

Reaction equation

HRID 53973 reaction equation
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]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 643448(S)-(-)-N-Boc-prolinol2×HCID 21844506Ethyl 3-(5-cyano-2-benzofuranyl)-2-(4-hydroxyphenyl)propionate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-46ff10ffd9214697abfcbbd0cfa3aa99
Source dataset
uspto-grants-1997_04
Patent number
US05620991

Linked notes

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