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Acetic Acid → (2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

HRID 1432929
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반응식

HRID 1432929 반응식
C(O)(=O)C.[N:5]1[CH:10]=[N:9][CH:8]=[N:7][CH:6]=1.[CH2:11]([O:18][C:19]([N:21]1[CH:26]([CH3:27])[CH2:25][N:24]([CH2:28][C:29]2[CH:34]=C[C:32](C#N)=[C:31](N)[CH:30]=2)[C:23](=[O:38])[C@@H:22]1[CH3:39])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>C(O)C>[CH2:11]([O:18][C:19]([N:21]1[CH:26]([CH3:27])[CH2:25][N:24]([CH2:28][C:29]2[CH:34]=[C:6]3[C:32]([C:10]([NH2:5])=[N:9][CH:8]=[N:7]3)=[CH:31][CH:30]=2)[C:23](=[O:38])[C@@H:22]1[CH3:39])=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 92621,3,5-TriazineHCID 57054342(2S,6RS)-4-(3-amino-4-cyano-benzyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

생성물 1

HCID 57166330(2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester수율 85.1%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

Glacial acetic acid (0.9 ml, 15.54 mmol) and 1,3,5-triazine (840 mg, 10.36 mmol) is added to a solution of (2S,6RS)-4-(3-amino-4-cyano-benzyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (2.03 g, 5.18 mmol) in ethanol. The resulting mixture is heated to reflux overnight. Replaced the ethanol with ethyl acetate and washed with saturated sodium bicarbonate (5 mL). The ethyl acetate layer is dried with magnesium sulfate, filtered and condensed. The resulting residue is purified by flash colunm (SiO2, 20% methanol/methylene chloride) to give the product (2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (1.85 g, 85%) as a yellow solid. C23H25N5O3 MS m/z: 420.

후처리

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux overnight
  3. washwashed with saturated sodium bicarbonate (5 mL)
  4. dry with materialThe ethyl acetate layer is dried with magnesium sulfate
  5. filtrationfiltered
  6. customcondensed
  7. customThe resulting residue is purified by flash colunm (SiO2, 20% methanol/methylene chloride)

출처 및 근거

ORD 기록
ord-5d393f2a70f241ca989619526d6e0e9f
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612075B2

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