Hydrochloric Acid → 3-(5-tert-Butyloxazol-4-yl)-N-((S)-1-carbamoyl-2-phenylethyl)-2-hydroxyacrylamide

HRID 15396

反応式

HRID 15396 の反応式
[C:1]([C:5]1[O:9][CH:8]=[N:7][C:6]=1[CH:10]=[C:11]([OH:15])[C:12]([OH:14])=O)([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl.Cl.[NH2:40][C@H:41]([C:49]([NH2:51])=[O:50])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CCN(CC)CC>CN(C=O)C>[C:1]([C:5]1[O:9][CH:8]=[N:7][C:6]=1[CH:10]=[C:11]([OH:15])[C:12]([NH:40][C@H:41]([C:49](=[O:50])[NH2:51])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:14])([CH3:2])([CH3:3])[CH3:4]

参加物

9

反応物 7

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 445694Phenylalanine amideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 665900433-(5-tert-Butyloxazol-4-yl)-2-hydroxyacrylic acid

生成物 1

HCID 665902203-(5-tert-Butyloxazol-4-yl)-N-((S)-1-carbamoyl-2-phenylethyl)-2-hydroxyacrylamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the compound from Example 6 (2.61 g, 12.3 mmol) in DMF were added HOBt.H2O (2.26 g, 14.76 mmol), EDC.HCl (2.8 g, 14.76 mmol), HCl.H-Phe-NH2 (3.16 g, 14.76 mmol) and Et3N (1.72 mL, 12.3 mmol) and the reaction mixture was stirred for 14 h at room temperature. After removal of the solvent, the residue was dissolved in AcOEt, successively washed with 10% citric acid, 5% NaHCO3 and saturated NaCl for three times, dried over Na2SO4, and concentrated in vacuo to obtain the title compound: yield 2.26 g (43%); mp 50-53° C., 1H NMR (300 MHz, CDCl3) δ 11.04 (s, 1H), 7.81 (d, J=0.6 Hz 1H), 7.74-7.21 (m, 5H), 6.62 (d, J=0.7 Hz 1H), 6.00 (s, 1H), 5.52 (s, 1H), 4.79-4.72 (m, 1H), 3.24-3.11 (m, 2H), 1.38 (s, 9H); HRMS (EI): m/z 357.1689 (M+) (calced for C19H23N3O4: 357.1688).

後処理

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in AcOEt
  3. washsuccessively washed with 10% citric acid, 5% NaHCO3 and saturated NaCl for three times
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2945833eb1554dbbbc24c16df5a3a8cf
出典データセット
uspto-grants-2010_06
特許番号
US07732605B2

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