1-Hydroxybenzotriazole → ((S)-1-{2-[(S)-2-(2-Benzyl-2H-tetrazol-5-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethylcarbamoyl}-propyl)-methyl-carbamic acid tert-butyl ester

HRID 29077노트

반응식

HRID 29077 반응식
[C:1]([O:5][C:6]([N:8]([CH3:15])[C@@H:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.[NH2:66][CH:67]([CH:87]1[CH2:92][CH2:91][CH2:90][CH2:89][CH2:88]1)[C:68]([N:70]1[CH2:74][CH2:73][CH2:72][C@H:71]1[C:75]1[N:76]=[N:77][N:78]([CH2:80][C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[N:79]=1)=[O:69]>CC(N(C)C)=O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[N:8]([C@H:9]([C:10](=[O:12])[NH:66][CH:67]([CH:87]1[CH2:88][CH2:89][CH2:90][CH2:91][CH2:92]1)[C:68]([N:70]1[CH2:74][CH2:73][CH2:72][C@H:71]1[C:75]1[N:76]=[N:77][N:78]([CH2:80][C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[N:79]=1)=[O:69])[CH2:13][CH3:14])[CH3:15])([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15689337(2S)-2-(((1,1-Dimethylethoxy)carbonyl)methylamino)butanoic acidHCID 866010842-amino-1-[(2S)-2-(2-benzyltetrazol-5-yl)pyrrolidin-1-yl]-2-cyclohexylethanone;2,2,2-trifluoroacetic acid

생성물 1

HCID 59788068((S)-1-{2-[(S)-2-(2-Benzyl-2H-tetrazol-5-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethylcarbamoyl}-propyl)-methyl-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 31374Dimethylacetamide용매

실험 절차

To a solution of (S)-2-(tert-butoxycarbonyl-methyl-amino)-butyric acid (53.0 mg, 0.24 mmol) in DMA (2 mL) is added HBTU (125.0 mg, 0.33 mmol), HOBt (44.6 mg, 0.33 mmol) and diisopropylethylamine (192 uL, 1.1 mmol). The mixture is stirred at room temperature for 5 minutes. A solution of compound F in DCM (2 mL) is added to the above mixture at 0° C. The reaction mixture is stirred at room temperature for 1 hour and concentrated under vacuum. The residue is diluted with EtOAc. The organic is washed with brine, citric acid(5%), brine, NaHCO3(Sat.) and brine. The organic layer is then dried and concentrated under vacuum. The crude oil is used directly in the next step without further purification. M+H+=554.

후처리

  1. stirringThe reaction mixture is stirred at room temperature for 1 hour
  2. concentrationconcentrated under vacuum
  3. additionThe residue is diluted with EtOAc
  4. washThe organic is washed with brine, citric acid(5%), brine, NaHCO3(Sat.) and brine
  5. customThe organic layer is then dried
  6. concentrationconcentrated under vacuum
  7. customThe crude oil is used directly in the next step without further purification

출처 및 근거

ORD 기록
ord-38c0671a2b8f44799303423205cf7513
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419975B2

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