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

HRID 361942

反応式

HRID 361942 の反応式
[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]

参加物

7

反応物 5

HCID 11776Triphenylphosphine2 回HCID 220568ethyl N-ethoxycarbonyliminocarbamate2 回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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fc438993a6284fe6b68269b96bba170a
出典データセット
uspto-grants-1999_02
特許番号
US05866577

関連ノート

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