Triphenylphosphine → (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-carbamic acid tert-butyl ester

HRID 902631노트

반응식

HRID 902631 반응식
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:16]1([CH:22]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:23][N:24]([CH2:37][CH2:38][CH2:39]O)[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[C:27]=2[Cl:36])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:39][CH2:38][CH2:37][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[C:27]=2[Cl:36])[CH2:23][CH:22]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamateHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

생성물 1

HCID 10175511(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-carbamic acid tert-butyl ester수율 59%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

To a stirring solution of N-(3-Hydroxy-phenyl)-carbamic acid tert-butyl ester (1.9 g, 9.0 mmol) in anhydrous toluene (60 mL) was added N-(2,2-diphenylethyl)-N-(3-hydroxy-propyl)-N-(2-chloro-3-trifluoromethyl-benzyl)amine (2.36 g, 5.3 mmol). Polymer bound triphenylphosphine (2.8 g, 8.4 mmol, 3 mmol/g, Fluka Chemie) was then added, and the mixture stirred for 15 minutes. The reaction mixture was then cooled to 0° C. and diisopropylazodicarboxylate (1.28 mL, 6.5 mmol) was added in a dropwise fashion. After stirring at room temperature for 60 hours, the crude reaction mixture was filtered and the resulting solid was washed with toluene. The filtrate was concentrated and the crude product was purified by silica gel chromatography (35 g Redisep column, silica, 40 um, 60 Å, 35 mL/min, A: hexanes, B: EtOAc, B: 0% for 5 min, B: 0% to 10% over 10 min; B: 10% for 10 min; B: 10% to 30% over 30 min; detection at 214 nm) to give 2.0 g (3.1 mmol, 59% yield) of the title compound as a white foam. MS (ESI) 639.4

후처리

  1. additionwas then added
  2. stirringAfter stirring at room temperature for 60 hours
  3. customthe crude reaction mixture
  4. filtrationwas filtered
  5. washthe resulting solid was washed with toluene
  6. concentrationThe filtrate was concentrated
  7. customthe crude product was purified by silica gel chromatography (35 g Redisep column, silica, 40 um, 60 Å, 35 mL/min
  8. waitA: hexanes, B: EtOAc, B: 0% for 5 min
  9. waitB: 0% to 10% over 10 min
  10. waitB: 10% for 10 min
  11. waitB: 10% to 30% over 30 min

출처 및 근거

ORD 기록
ord-b55d766fe3bf4201b4297d076e285f93
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365085B2

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