Trifluoroacetic acid → tert-butyl 2-(4-amino-N-(4-(3-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate

HRID 923606

反応式

HRID 923606 の反応式
C(OC([NH:8][C:9]1[CH:50]=[CH:49][C:12]([C:13]([N:15]([CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[O:27][N:26]=[C:25]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=5)=[CH:30][CH:29]=4)[N:24]=3)=[CH:19][CH:18]=2)=[O:14])=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:8][C:9]1[CH:50]=[CH:49][C:12]([C:13]([N:15]([CH2:41][C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[O:27][N:26]=[C:25]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=5)=[CH:30][CH:29]=4)[N:24]=3)=[CH:21][CH:22]=2)=[O:14])=[CH:11][CH:10]=1

参加物

5

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 71111627tert-butyl 2-(4-((tert-butoxycarbonyl)amino)-N-(4-(3-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate

生成物 1

HCID 89284665tert-butyl 2-(4-amino-N-(4-(3-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate収率 50%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

Prepared using General Procedure 8. To a stirred solution of tert-butyl 2-(4-((tert-butoxycarbonyl)amino)-N-(4-(3-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate INT-63 (659 mg, 0.977 mmol) in DCM (15 mL) was added TFA (752 μL, 9.77 mmol) at room temperature. After 2 h additional TFA (752 μL, 9.77 mmol) was added and the reaction mixture stirred for a further 3 h at room temperature. The reaction mixture was diluted with toluene (20 mL) and the solvent removed in vacuo. The residue was diluted with EA (100 mL) and washed with NaHCO3 (30 mL). The organics were concentrated in vacuo and the crude product was purified by chromatography (EA/hexanes) to afford 284 mg (50%) of tert-butyl 2-(4-amino-N-(4-(3-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate INT-64 as an off-white powder. LCMS-ESI (m/z) calculated for C35H34N4O4: 574; found 519 [M-t-Bu+H]+, 573 [M−H]−, tR=3.12 min (Method 10).

後処理

  1. customPrepared
  2. customthe solvent removed in vacuo
  3. additionThe residue was diluted with EA (100 mL)
  4. washwashed with NaHCO3 (30 mL)
  5. concentrationThe organics were concentrated in vacuo
  6. customthe crude product was purified by chromatography (EA/hexanes)

出典と根拠

ORDレコード
ord-8e64073729534d05a4d7f99cbc840817
出典データセット
uspto-grants-2016_03
特許番号
US09278910B2

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