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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → (3-Carbamoyl-1-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-1H-indol-6-yloxy)-acetic acid methyl ester

HRID 1527573
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HRID 1527573 반응식
[Cl:1][C:2]1[C:3]([F:34])=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][NH:6][C:7]([C@@H:9]1[CH2:13][C@@H:12]([F:14])[CH2:11][N:10]1[C:15](=[O:30])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([OH:26])[CH:24]=2)[C:19]([C:27]([NH2:29])=[O:28])=[CH:18]1)=[O:8].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:42][C:43]([O:45][CH3:46])=[O:44]>CS(C)=O>[CH3:46][O:45][C:43](=[O:44])[CH2:42][O:26][C:23]1[CH:24]=[C:25]2[C:20]([C:19]([C:27](=[O:28])[NH2:29])=[CH:18][N:17]2[CH2:16][C:15]([N:10]2[CH2:11][C@H:12]([F:14])[CH2:13][C@H:9]2[C:7](=[O:8])[NH:6][CH2:5][C:4]2[CH:31]=[CH:32][CH:33]=[C:2]([Cl:1])[C:3]=2[F:34])=[O:30])=[CH:21][CH:22]=1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 682831451-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-6-hydroxy-1H-indole-3-carboxylic acid amide

생성물 1

HCID 68283320(3-Carbamoyl-1-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-1H-indol-6-yloxy)-acetic acid methyl ester

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

실험 절차

A solution of 1-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-6-hydroxy-1H-indole-3-carboxylic acid amide Example 578 (140 mg, 0.285 mmol) in DMSO (3 mL) was treated with Cs2CO3 (0.28 g, 0.85 mmol). The mixture was stirred at RT for 5 min, followed by addition of methyl 2-bromoacetate (0.039 mL, 0.428 mmol) and stirring at RT for 4 h. The mixture was partitioned between water and CH2Cl2, and the organic phase was washed twice with brine (the combined aqueous washings were filtered and the solid thus obtained was dried in vacuo to give an aliquot of the title compound), dried (phase separator) and concentrated under reduced pressure. Purification by preparative HPLC (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) afforded after lyophilization of the purified fractions the title compound as a white solid. MS: 563 [M+H]+; tR (HPLC conditions c): 4.17 min.

후처리

  1. stirringstirring at RT for 4 h
  2. customThe mixture was partitioned between water and CH2Cl2
  3. washthe organic phase was washed twice with brine (the combined aqueous washings
  4. filtrationwere filtered
  5. customthe solid thus obtained
  6. customwas dried in vacuo

출처 및 근거

ORD 기록
ord-1ea71285de464dc5985b71d00cbc3a92
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085555B2

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