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

HRID 333346ノート

反応式

HRID 333346 の反応式
[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

参加物

7

反応物 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)

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-044dd0e83af8456b9f3fddbd3c1136ea
出典データセット
uspto-grants-2014_11
特許番号
US08877815B2

反応ノート

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