Triphenylphosphine → ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)thio]phenyl]acetate

HRID 53980

반응식

HRID 53980 반응식
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:25][CH2:24][C@@H:23](O)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:14]([O:18][C:19]([N:21]1[CH2:25][CH2:24][C@H:23]([S:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=2)[CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylateHCID 123300434-Mercapto-phenyl-acetic acid ethyl ester

생성물 1

HCID 57063129ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)thio]phenyl]acetate수율 18.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

20.2 g of ethyl 4-mercaptophenylacetate was dissolved in 450 ml of tetrahydrofuran. With ice cooling and with stirring, 21.0 g of (3R)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine, 29.4 g of triphenylphosphine and 19.5 g of diethyl azodicarboxylate were added to the above solution. The thus prepared mixture was stirred at room temperature for 18 hours. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using a n-hexane/ethyl acetate mixture as an elution solvent, thereby obtaining 7.0 g of ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)thio]phenyl]acetate.

후처리

  1. stirringThe thus prepared mixture was stirred at room temperature for 18 hours
  2. distillationAfter distilling off the solvent
  3. customthe resulting residue was purified

출처 및 근거

ORD 기록
ord-d20234f951904d76b671f58a88354903
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620991

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