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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
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HRID 717653 반응식
[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]
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f64cc14936e47a596efabe683bdcd07
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193716B2

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