1,2-Dichloroethane → (R)-N-(tert-Butoxycarbonyl)-4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine

HRID 1191045ノート

反応式

HRID 1191045 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:42][C@@H:43]([NH2:48])[C:44]([F:47])([F:46])[F:45]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17](=[O:19])[NH:48][C@H:43]([CH3:42])[C:44]([F:47])([F:46])[F:45])=[CH:14][CH:15]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27559832-(4-((((Tert-butoxy)carbonyl)amino)methyl)phenyl)acetic acidHCID 44593757(R)-2-Amino-1,1,1-trifluoropropane hydrochloride

生成物 1

HCID 58495584(R)-N-(tert-Butoxycarbonyl)-4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine収率 68.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Dissolve [4-(tert-butoxycarbonylamino-methyl)-phenyl]-acetic acid (190 mg, 0.63 mmol) in DCM (12.4 mL) and add triethylamine (354 μL, 2.5 mmol), DMAP (8 mg, 0.063 mmol), EDC (145 mg, 0.756 mmol), HOBt (102 mg, 0.756 mmol) and (R)-1-methyl-2,2,2-trifluoro-ethylamine hydrochloride (71 mg, 0.63 mmol) under nitrogen atmosphere. Stir the reaction overnight at room temperature. Concentrate in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (1:1 and 0:1) to obtain the desired intermediate (155 mg, 68%).

後処理

  1. customthe reaction overnight at room temperature
  2. concentrationConcentrate in vacuo
  3. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:1 and 0:1)

出典と根拠

ORDレコード
ord-326b17d185d1400195a1aee386bf9c84
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

読み込み中…