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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Diisopropylethylamine → {(1R,3S,5R)-2-[2-(3-Acetyl-indol-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hex-3-ylmethyl}-carbamic acid 3-chloro-2-fluoro-phenyl ester

HRID 1527589
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HRID 1527589 반응식
[Cl:1][C:2]1[C:3]([F:19])=[C:4]([O:8][C:9](=[O:18])[NH:10][CH2:11][C@@H:12]2[CH2:17][C@@H:16]3[C@@H:14]([CH2:15]3)[NH:13]2)[CH:5]=[CH:6][CH:7]=1.ClC1C(F)=C(OC(=O)NC[C@@H]2C[C@@H]3[C@@H](C3)N2C(=O)NC2C3C(=CC=CC=3)N(C(=O)N)C=2)C=CC=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:87]([C:90]1[C:98]2[C:93](=[CH:94][CH:95]=[CH:96][CH:97]=2)[N:92]([CH2:99][C:100](O)=[O:101])[CH:91]=1)(=[O:89])[CH3:88]>C1COCC1>[Cl:1][C:2]1[C:3]([F:19])=[C:4]([O:8][C:9](=[O:18])[NH:10][CH2:11][C@@H:12]2[CH2:17][C@@H:16]3[C@@H:14]([CH2:15]3)[N:13]2[C:100](=[O:101])[CH2:99][N:92]2[C:93]3[C:98](=[CH:97][CH:96]=[CH:95][CH:94]=3)[C:90]([C:87](=[O:89])[CH3:88])=[CH:91]2)[CH:5]=[CH:6][CH:7]=1
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참가 물질

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반응물 5

HCID 81531DiisopropylethylamineHCID 1088616(3-Acetyl-indol-1-yl)-acetic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68283648[(1R,3S,5R)-2-(1-Carbamoyl-1H-indol-3-ylcarbamoyl)-2-aza-bicyclo[3.1.0]hex-3-ylmethyl]-carbamic acid 3-chloro-2-fluoro-phenyl esterHCID 68283842
[(1R,3S,5R)-1-(2-aza-bicyclo[3.1.0]hex-3-yl)methyl]-carbamic acid 3-chloro-2-fluoro-phenyl ester

생성물 1

HCID 68283594{(1R,3S,5R)-2-[2-(3-Acetyl-indol-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hex-3-ylmethyl}-carbamic acid 3-chloro-2-fluoro-phenyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of [(1R,3S,5R)-1-(2-aza-bicyclo[3.1.0]hex-3-yl)methyl]-carbamic acid 3-chloro-2-fluoro-phenyl ester, trifluoroacetate (prepared as described in Example 115) (60.0 mg, 0.211 mmol) in THF (3 mL) was added HBTU (120 mg, 0.316 mmol), DIPEA (0.147 mL, 0.843 mmol) and (3-acetyl-indol-1-yl)-acetic acid (50 mg, 0.232 mmol). The reaction mixture was stirred at RT for 60 h. Volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, eluent: 20-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min) to give after lyophilization of the purified HPLC fractions the title compound. MS (LC/MS): 484.0 [M+H]+; tR (HPLC conditions k): 3.69 min.

후처리

  1. customVolatiles were removed under reduced pressure
  2. customthe residue was purified by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, eluent: 20-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min)

출처 및 근거

ORD 기록
ord-ec3b2d406c1e449fabb8af88c572e3d0
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085555B2

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