Triphenylphosphine → 5-{4-[2(R)-t-butoxycarbonylaminopropoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione

HRID 1901225노트

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HRID 1901225 반응식
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][C:33]1[CH:65]=[CH:64][C:36]([CH2:37][CH:38]2[S:42][C:41](=[O:43])[N:40]([C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]2=[O:63])=[CH:35][CH:34]=1.[C:66]([O:70][C:71]([NH:73][C@H:74]([CH3:77])[CH2:75]O)=[O:72])([CH3:69])([CH3:68])[CH3:67]>C1C=CC=CC=1>[C:66]([O:70][C:71]([NH:73][C@H:74]([CH3:77])[CH2:75][O:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:37][CH:38]2[S:42][C:41](=[O:43])[N:40]([C:44]([C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:39]2=[O:63])=[CH:64][CH:65]=1)=[O:72])([CH3:69])([CH3:68])[CH3:67]

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate2회

생성물 1

HCID 228549855-{4-[2(R)-t-butoxycarbonylaminopropoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione수율 64.1%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

13.2 g of diethyl azodicarboxylate were added dropwise to a solution of 20.7 g of triphenylphosphine in 300 ml of benzene and the mixture was stirred at room temperature for 30 minutes. At the end of this time, 35.0 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione [prepared as described in step (d) above] were added to the mixture, and the resulting mixture was stirred at room temperature for 1 hour. 13.2 g of (R)-2-t-butoxycarbonylamino-1-propanol were added to the mixture, which was then allowed to stand overnight. At the end of this time, 40.9 g of triphenylphosphine, 23.68 ml of diethyl azodicarboxylate and 33 g of (R)-2-t-butoxycarbonylamino-1-propanol were added to the reaction mixture, in that order, in 3 or 4 separate portions, and the mixture was then stirred for 2 days. After this time, the benzene solvent was removed from the reaction mixture by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1: 3 by volume mixture of ethyl acetate and hexane as the eluent, to give 30 g of the title compound as crystals, melting at 153°-157° C.

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. waitto stand overnight
  3. customseparate portions
  4. stirringthe mixture was then stirred for 2 days
  5. customAfter this time, the benzene solvent was removed from the reaction mixture by distillation under reduced pressure
  6. customthe residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and hexane as the eluent

출처 및 근거

ORD 기록
ord-c4e69017ce97433a845fd725c062d157
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576340

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