Hydrochloric Acid → 1-[(3-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carbonyl)-amino]-2-vinyl-cyclo-propane carboxylic acid ethyl ester

HRID 1429152ノート

反応式

HRID 1429152 の反応式
[O:1]=[C:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH:6]2[C:9]([OH:11])=O)[O:3]1.Cl.[CH2:13]([O:15][C:16]([C:18]1([NH2:23])[CH2:20][CH:19]1[CH:21]=[CH2:22])=[O:17])[CH3:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[CH2:13]([O:15][C:16]([C:18]1([NH:23][C:9]([CH:6]2[CH2:5][CH:4]3[CH2:8][CH:7]2[C:2](=[O:1])[O:3]3)=[O:11])[CH2:20][CH:19]1[CH:21]=[CH2:22])=[O:17])[CH3:14]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22082824Ethyl 1-amino-2-vinylcyclopropanecarboxylateHCID 462449653-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid

生成物 1

HCID 668704341-[(3-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carbonyl)-amino]-2-vinyl-cyclo-propane carboxylic acid ethyl ester収率 99%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of compound 3b (857 mg, 5.5 mmol), in DMF (14 mL) and DCM (25 mL) at room temperature, was added the hydrochloride of 1-amino-2-vinyl-cyclopropanecarboxylic acid ethyl ester, prepared as described in WO03/099274, (1.15 g, 6.0 mmol), HATU (2.29 g, 6.0 mmol) and DIPEA (3.82 mL, 22 mmol). The reaction was stirred under N2-atmosphere at ambient temperature for 1 h. LC/MS analysis showed complete conversion and the reaction mixture was concentrated in vacuo. The residue was redissolved in DCM (100 ml) and 0.1 M HCl (aq) and the phases were separated. The organic phase was washed with NaHCO3 (aq) and brine, dried (MgSO4) and filtered. Removal of the solvent in vacuo afforded the target compound (1.6 g, 99%). LC/MS >95%, m/z (ESI+)=294 (MH+)

後処理

  1. customprepared
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was redissolved in DCM (100 ml)
  4. custom0.1 M HCl (aq) and the phases were separated
  5. washThe organic phase was washed with NaHCO3 (aq) and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customRemoval of the solvent in vacuo

出典と根拠

ORDレコード
ord-46a00263fddc4db98f02531c98777395
出典データセット
uspto-grants-2015_01
特許番号
US08937080B2

反応ノート

読み込み中…