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Triethylamine → tert-Butyl {5-[{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}(methyl)carbamoyl]-2-thienyl}carbamate

HRID 446502
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HRID 446502 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[F:31][C:32]([F:85])([F:84])[C:33]1[CH:34]=[C:35]([CH:77]=[C:78]([C:80]([F:83])([F:82])[F:81])[CH:79]=1)[C:36]([N:38]1[CH2:42][C@@:41]([CH2:50][CH2:51][N:52]2[CH2:57][CH2:56][C:55]3([C:65]4[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=4)[CH2:59][C@@H:58]3[O:66][CH2:67][C:68]([N:70]([CH3:76])[CH2:71][CH2:72][CH2:73][NH:74][CH3:75])=[O:69])[CH2:54][CH2:53]2)([C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)[O:40][CH2:39]1)=[O:37]>C(Cl)Cl>[F:83][C:80]([F:81])([F:82])[C:78]1[CH:77]=[C:35]([CH:34]=[C:33]([C:32]([F:31])([F:85])[F:84])[CH:79]=1)[C:36]([N:38]1[CH2:42][C@@:41]([CH2:50][CH2:51][N:52]2[CH2:53][CH2:54][C:55]3([C:65]4[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=4)[CH2:59][C@@H:58]3[O:66][CH2:67][C:68]([N:70]([CH3:76])[CH2:71][CH2:72][CH2:73][N:74]([CH3:75])[C:14]([C:12]3[S:13][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:10][CH:11]=3)=[O:16])=[O:69])[CH2:56][CH2:57]2)([C:43]2[CH:44]=[CH:45][C:46]([F:49])=[CH:47][CH:48]=2)[O:40][CH2:39]1)=[O:37]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 221055695-(((Tert-butoxy)carbonyl)amino)thiophene-2-carboxylic acidHCID 866634192-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-[3-(methylamino)propyl]acetamide

생성물 1

HCID 86663425
tert-Butyl {5-[{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}(methyl)carbamoyl]-2-thienyl}carbamate
수율 94.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The compound (94 mg, 0.385 mmol) obtained in Example 4c was dissolved in methylene chloride (4 mL), triethylamine (80 μL, 0.578 mmol) and pivaloyl chloride (52 μL, 0.424 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. The compound (300 mg, 0.385 mmol) obtained in Example 1k was added to the reaction mixture under ice cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v) to give the title compound (366 mg; yield, 94%) as a white solid.

후처리

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v)

출처 및 근거

ORD 기록
ord-4f4334251065464988c1d45db41cc2d7
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08476253B2

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