Dimethylamine → tert-butyl[(1S)-1-(biphenyl-4-ylmethyl)-2-(dimethylamino)-2-oxoethyl]carbamate

HRID 333346노트

반응식

HRID 333346 반응식
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:9](O)=[O:10])=[CH:3][CH:2]=1.[CH3:26][N:27](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:28].F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.CNC>CN(C=O)C.C(Cl)Cl>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:9]([N:27]([CH3:28])[CH3:26])=[O:10])=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 2761796N-alpha-t-Butyloxycarbonyl-L-biphenylalanine (Boc-L-Bip-OH)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 59496665tert-butyl[(1S)-1-(biphenyl-4-ylmethyl)-2-(dimethylamino)-2-oxoethyl]carbamate수율 60.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-3-(biphenyl-4-yl)-2-(tert-butoxycarbonylamino)propanoic acid (300 mg, 0.88 mmol) in DMF (1.5 mL) and DCM (1.5 mL) was added HATU (401 mg, 1.05 mmol) and triethylamine (0.37 mL, 2.64 mmol). To the mixture at room temperature was added dimethylamine (0.46 mL, 0.91 mmol). The mixture was stirred at room temperature for 2 hours, quenched with sat NaHCO3, and extracted with EtOAc. The organic layer was washed with water (8 times), brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by TLC preparation plates using 5% 2M Ammonia in MeOH and DCM to give (S)-tert-butyl 3-(biphenyl-4-yl)-1-(dimethylamino)-1-oxopropan-2-ylcarbamate (196 mg). HPLC retention time=1.66 minutes (condition B); MS (m+1)=369.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.37 (s, 9H) 2.65 (s, 3H) 2.83 (s, 3H) 2.96 (d, J=7.1 Hz, 2H) 4.71-4.94 (m, 1H) 5.56 (d, J=8.6 Hz, 1H) 7.22 (d, J=8.1 Hz, 2H) 7.27 (t, J=7.5 Hz, 1H) 7.37 (t, J=7.6 Hz, 2H) 7.47 (d, J=8.1 Hz, 2H) 7.52 (d, J=7.3 Hz, 2H).

후처리

  1. customquenched with sat NaHCO3
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water (8 times), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by TLC preparation plates

출처 및 근거

ORD 기록
ord-044dd0e83af8456b9f3fddbd3c1136ea
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877815B2

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