Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane → tert-butyl (R)-3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-hydroxypropylcarbamate

HRID 1189969노트

반응식

HRID 1189969 반응식
[C:1]([O:5][C:6]([N:8]([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:9]1[CH:10]=[C:11]([C:15](=[O:26])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1)[C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:27][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)[C:9]1[CH:10]=[C:11]([C@H:15]([OH:26])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

4

반응물 2

HCID 9923113Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)boraneHCID 68524283Tert-butyl 3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-oxopropylcarbamate

생성물 1

HCID 86641455tert-butyl (R)-3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-hydroxypropylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of tert-butyl 3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-oxopropylcarbamate and (+)-Ipc2BCl in anhydrous THF is stirred at room temperature until no starting material is seen by TLC. The reaction is then quenched with aqueous NH4Cl and stirred at room temperature. Extraction with EtOAc and drying over anhydrous MgSO4 followed by flash chromatography (EtOAc—hexanes gradient) gives tert-butyl (R)-3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-hydroxypropylcarbamate.

후처리

  1. customThe reaction is then quenched with aqueous NH4Cl
  2. stirringstirred at room temperature
  3. extractionExtraction with EtOAc
  4. dry with materialdrying over anhydrous MgSO4

출처 및 근거

ORD 기록
ord-dafcf108c24d41ca90094491f341e634
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674137B2

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