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Glycine, N-methyl-, hydrochloride (1:1) → Methyl-2-((4-(5-(((4-fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzyl)(methyl)amino)acetate

HRID 717653
ノート
印刷プレビュー

反応式

HRID 717653 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:12][C:13]2[S:17][C:16]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=3)=[CH:15][CH:14]=2)[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.Cl.[NH:27]([CH2:29][C:30]([OH:32])=[O:31])[CH3:28].[CH3:33]CN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CC(O)=O.C(Cl)Cl>[CH3:33][O:31][C:30](=[O:32])[CH2:29][N:27]([CH2:22][C:21]1[CH:24]=[CH:25][C:18]([C:16]2[S:17][C:13]([CH2:12][N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:9]([CH3:11])[CH3:10])=[CH:14][CH:15]=2)=[CH:19][CH:20]=1)[CH3:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866606114-(5-(((4-Fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde

生成物 1

HCID 66615086Methyl-2-((4-(5-(((4-fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzyl)(methyl)amino)acetate収率 100%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of the product of Step B (0.09 g, 0.26 mmol) and sarcosine hydrochloride (0.07 g, 0.5 mmol) in 1,2-dichloroethane (5 ml) was added DIPEA (0.1 ml) and 10 drops of AcOH, followed by NaBH(OAc)3 (0.11 g, 0.51 mmol). The mixture was stirred overnight at room temperature and diluted to 20 ml with CH2Cl2. The organic layer was washed with NaHCO3 solution, H2O and dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.113 g, 100%) as creamy paste. 1H-NMR (CDCl3) 7.47 (d, 2H, J=8.19 Hz); 7.28 (d, 2H, J=8.18 Hz); 7.10 (d, 1H, J=3.62 Hz); 6.88-6.85 (m, 3H); 6.85-6.77 (m, 2H); 4.44 (s, 2H); 4.07-3.98 (m, 1H); 3.69 (s, 3H); 3.24 (s, 2H); 2.37 (s, 3H); 1.21 (d, 6H, J=6.6 Hz).

後処理

  1. washThe organic layer was washed with NaHCO3 solution, H2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by FCC (SiO2, hexane/EtOAc)

出典と根拠

ORDレコード
ord-7f64cc14936e47a596efabe683bdcd07
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09193716B2

反応ノート

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