Methyl 4-(bromomethyl)benzoate → Methyl 4-{3-tert-butoxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}benzoate

HRID 1919898

반응식

HRID 1919898 반응식
[C:1]([O:5][C:6](=[O:16])[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Br[CH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:16])[CH:7]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1)([CH3:3])([CH3:4])[CH3:2]

참가 물질

6

반응물 3

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 2733832Lithium HexamethyldisilazideHCID 4097102tert-Butyl ((tert-butoxycarbonyl)amino)acetate

생성물 1

HCID 57611911Methyl 4-{3-tert-butoxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}benzoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

Tert-butyl[(tert-butoxycarbonyl)amino]acetate (1.01 g, 4.37 mmol) was dissolved in THF (10 mL) and cooled to −78° C. LiHMDS (6.5 mL, 1M solution in THF) was slowly added and allowed to stir for 30 minutes. Methyl 4-(bromomethyl)benzoate (1.98 g, 8.64 mmol) in THF (6 mL) was added to the mixture and allowed to stir overnight, slowly warming to room temperature. The reaction was diluted with ethyl acetate and quenched with saturated ammonium chloride. The aqueous layer was extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by column chromatography. MS: cal'd 379 (MH+), exp 402 (MH+).

후처리

  1. stirringto stir overnight
  2. temperatureslowly warming to room temperature
  3. customquenched with saturated ammonium chloride
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-fd8c5cc610c84a5b9d787fb783e8e6d1
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168658B2

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