Hydrochloric Acid → O-[3-(allyloxycarbonyl)-benzyl]-N-(t-butoxycarbonyl)-L-serine

HRID 2414370노트

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HRID 2414370 반응식
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].I[CH2:18][C:19]1[CH:20]=[C:21]([CH:28]=[CH:29][CH:30]=1)[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23].Cl>CN(C=O)C>[CH2:25]([O:24][C:22]([C:21]1[CH:20]=[C:19]([CH:30]=[CH:29][CH:28]=1)[CH2:18][O:13][CH2:12][C@@H:11]([C:14]([OH:16])=[O:15])[NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])=[O:23])[CH:26]=[CH2:27]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 11808802Allyl 3-iodomethylbenzoate

생성물 1

HCID 54022019O-[3-(allyloxycarbonyl)-benzyl]-N-(t-butoxycarbonyl)-L-serine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

Sodium hydride (19.4 g, 60% in mineral oil, 484.4 mmol) is washed with dry hexanes (2×30 mL) to remove the mineral oil and then suspended in anhydrous DMF (330 mL). To this suspension a solution of N-(t-butoxycarbonyl)-L-serine (45.2 g, 220.2 mmol) in DMF (110 mL) at 0° C. is added dropwise with vigorous stirring. The mixture is stirred for an additional 5 minutes at 0° C., and then at room temperature for 30 minutes. The solution is cooled back to 0° C., and a solution of allyl 3-iodomethylbenzoate (66.6 g, 220.2 mmol) in DMF (110 mL) is added dropwise over 15 minutes. The mixture is then warmed to room temperature for 30 minutes. The reaction mixture is poured into ice water (2.2 L) and acidified to pH 2 with 1 N HCl (270 mL). The mixture is extracted with ether (1×600 mL, then 3×300 mL) and the combined ether extracts are then washed with water (5×200 ml) and then dried (MgSO4) and evaporated in vacuo to yield O-[3-(allyloxycarbonyl)-benzyl]-N-(t-butoxycarbonyl)-L-serine as a yellowish oil.

후처리

  1. customto remove the mineral oil
  2. waitat room temperature for 30 minutes
  3. temperatureThe solution is cooled back to 0° C.
  4. temperatureThe mixture is then warmed to room temperature for 30 minutes
  5. extractionThe mixture is extracted with ether (1×600 mL
  6. wash3×300 mL) and the combined ether extracts are then washed with water (5×200 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-80ffa4329d0346dfb8adddee08ca4641
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06812237B2

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