Triphenylphosphine → ethyl 2-[4-[((2R)-2-tert-butoxycarbonylamino-1-butyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate

HRID 1901376

Reaction equation

HRID 1901376 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][CH:12]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][C:7]=2[CH:25]=1)#[N:2].C(OC([C@H](CC)C(N)O)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:70]([O:74][C:75]([NH:77][C@H:78]([CH2:81][CH3:82])[CH2:79]O)=[O:76])([CH3:73])([CH3:72])[CH3:71]>O1CCCC1>[C:70]([O:74][C:75]([NH:77][C@H:78]([CH2:81][CH3:82])[CH2:79][O:24][C:21]1[CH:20]=[CH:19][C:18]([CH:12]([CH2:11][C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:25][C:7]=3[CH:8]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:23][CH:22]=1)=[O:76])([CH3:73])([CH3:72])[CH3:71]

Participants

7

Reactant 5

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 11435422N-Boc-(R)-(+)-2-amino-1-butanolHCID 21844506Ethyl 3-(5-cyano-2-benzofuranyl)-2-(4-hydroxyphenyl)propionateHCID 86750019(2R)-2-tert-butoxycarbonyl-amino-1-butanol

Product 1

HCID 53858426ethyl 2-[4-[((2R)-2-tert-butoxycarbonylamino-1-butyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionateYield 39.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 300 ml of tetrahydrofuran were dissolved 1.1 g of ethyl 3-(5-cyano-2-benzofuranyl)-2-(4-hydroxyphenyl)propionate, 1.24 g of (2R)-2-tert-butoxycarbonyl-amino-1-butanol and 1.72 g of triphenylphosphine. The thus prepared solution was mixed with 1.14 g of diethyl azodicarboxylate and stirred at room temperature for 18 hours. The resulting solution was further mixed with 0.83 g of (2R)-2-tert-butoxycarbonylamino-1-butanol, 1.2 g of triphenylphosphine and 0.76 g of diethyl azodicarboxylate, and the mixture was stirred at room temperature for 18 hours. After concentrating the thus prepared reaction solution to dryness, the resulting residue was purified by subjecting it to silica gel column chromatography using a toluene/ethyl acetate mixture as a developing solvent, thereby obtaining 660 mg of ethyl 2-[4-[((2R)-2-tert-butoxycarbonylamino-1-butyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate in a colorless and oily form.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. concentrationAfter concentrating
  3. customthe thus prepared reaction solution to dryness
  4. customthe resulting residue was purified

Sources & evidence

ORD record
ord-1c21f49fa0cc4c05ab8643951790ce07
Source dataset
uspto-grants-1996_11
Patent number
US05576343

Linked notes

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