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Dicyclohexylcarbodiimide → 4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)-N-(2-(methylsulfonamido)-2-oxoethyl)benzamide

HRID 923616
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HRID 923616 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:50]=[CH:49][C:16]([C:17]([N:19]([CH2:45][C:46](O)=[O:47])[CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[N:31]=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([C:38]6[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=6)=[CH:34][CH:33]=5)[O:29][N:28]=4)=[CH:23][CH:22]=3)=[O:18])=[CH:15][CH:14]=2)=[O:11])=[C:5]([C:51]([F:54])([F:53])[F:52])[CH:4]=1.[CH3:55][S:56]([NH2:59])(=[O:58])=[O:57].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([N:19]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]4[N:31]=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([C:38]6[CH:39]=[CH:40][C:41]([CH3:44])=[CH:42][CH:43]=6)=[CH:34][CH:33]=5)[O:29][N:28]=4)=[CH:25][CH:26]=3)[CH2:45][C:46]([NH:59][S:56]([CH3:55])(=[O:58])=[O:57])=[O:47])=[O:18])=[CH:49][CH:50]=2)=[O:11])=[C:5]([C:51]([F:53])([F:54])[F:52])[CH:4]=1
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참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 72879MethanesulfonamideHCID 711116302-(4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetic acid

생성물 1

HCID 710781694-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)-N-(2-(methylsulfonamido)-2-oxoethyl)benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 2-(4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetic acid 354 (15 mg, 0.02 mmol), methanesulfonamide (2.9 mg, 0.03 mmol) and N,N-dimethylaminopyridine (5 mg, 0.04 mmol) in anhydrous DCM (1 mL) was added dicylcohexylcarbodiimide (6.3 mg). The reaction mixture was stirred at room temperature for 12 h. The reaction was diluted with DCM (2 mL) and washed with saturated NaHCO3 solution (5 mL), brine (5 mL), dried over (MgSO4) then concentrated. The crude product was isolated by HPLC to afford 4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)-N-(2-(methylsulfonamido)-2-oxoethyl)benzamide 493. LCMS-ESI (m/z) calculated for C42H36F3N5O7S: 812; no ion observed, tR=11.03 min (Method 2).

후처리

  1. washwashed with saturated NaHCO3 solution (5 mL), brine (5 mL)
  2. dry with materialdried over (MgSO4)
  3. concentrationthen concentrated
  4. customThe crude product was isolated by HPLC

출처 및 근거

ORD 기록
ord-ed6390369aa744628d65ecd02ab470e3
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278910B2

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