Ethyl Acetate → (1,1-dimethylethyl) 3-[[6-[4-(methoxycarbonyl)-1-piperidinyl]-5-methyl-4-pyrimidinyl]amino]-N-[(phenylmethoxy)carbonyl]alaninate

HRID 729743ノート

反応式

HRID 729743 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][C@@H:10]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C:3]=1[CH3:29].[NH:30]1[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH3:39])=[O:37])[CH2:32][CH2:31]1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O>[CH3:39][O:38][C:36]([CH:33]1[CH2:34][CH2:35][N:30]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][C@@H:10]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[NH:11][C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C:3]=2[CH3:29])[CH2:31][CH2:32]1)=[O:37]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 424914Methyl isonipecotateHCID 516892Sodium BicarbonateHCID 12094347(1,1-Dimethylethyl)-3-[(6-chloro-5-methyl-4-pyrimidinyl)amino]-n-[(phenylmethoxy)carbonyl]alaninate

生成物 1

HCID 12094348(1,1-dimethylethyl) 3-[[6-[4-(methoxycarbonyl)-1-piperidinyl]-5-methyl-4-pyrimidinyl]amino]-N-[(phenylmethoxy)carbonyl]alaninate収率 25%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 80 mg (0.19 mmoles) of (1,1-dimethylethyl) 3-[(6-chloro-5-methyl-4-pyrimidinyl)amino]-N-[(phenylmethoxy) carbonyl]alaninate and 3 ml of methyl 4-piperidinylcarboxylate is heated under reflux for 3 hours. After cooling down the reaction medium is taken up in water, ethyl acetate and a saturated solution of sodium bicarbonate. The organic phase is separated and the aqueous phase reextracted with ethyl acetate. The combined organic phases are dried over magnesium sulphate then the solvent eliminated under vacuum. The residue is chromatographed on silicagel eluting with a gradient of heptane (100%) to heptane-ethyl acetate (50-50). 25 mg (Yield=25%) of the expected product is obtained in the form of oil.

後処理

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling down the reaction medium
  4. customThe organic phase is separated
  5. dry with materialThe combined organic phases are dried over magnesium sulphate
  6. customThe residue is chromatographed
  7. washon silicagel eluting with a gradient of heptane (100%) to heptane-ethyl acetate (50-50)

出典と根拠

ORDレコード
ord-ef2a2387e6b74388b3df79b31afcd2ac
出典データセット
uspto-grants-2009_09
特許番号
US07582640B2

反応ノート

読み込み中…