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Hydrochloric Acid → N-[(2-Adamantyloxy)carbonyl]-alpha-trimethylsilylethoxymethyl-DL-tryptophan

HRID 1198086
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HRID 1198086 반응식
C[O:2][C:3](=[O:37])[CH:4]([CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)[N:5]([CH2:19][O:20][CH:21]([Si:23]([CH3:26])([CH3:25])[CH3:24])[CH3:22])[C:6]([O:8][CH:9]1[CH:16]2[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:18][CH:10]1[CH2:11]3)[CH2:15]2)=[O:7].[Li+].[OH-].O1CCOCC1.Cl>O>[CH:10]12[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15][CH:16]([CH2:17]3)[CH:9]1[O:8][C:6]([N:5]([CH2:19][O:20][CH:21]([Si:23]([CH3:25])([CH3:24])[CH3:26])[CH3:22])[CH:4]([C:3]([OH:37])=[O:2])[CH2:27][C:28]1[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][CH:29]=1)=[O:7])[CH2:18]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 86747503N-[(2-Adamantyloxy)carbonyl]-alpha-trimethylsilylethoxymethyl-DL-tryptophan methyl ester

생성물 1

HCID 86747505N-[(2-Adamantyloxy)carbonyl]-alpha-trimethylsilylethoxymethyl-DL-tryptophan수율 91.8%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A mixture of N-[(2-adamantyloxy)carbonyl]-α-trimethylsilylethoxymethyl-DL-tryptophan methyl ester (4.5 g, 8.5 mmol), LiOH (0.22 g, 9.1 mmol), dioxane (90 mL), and water (30 mL) was stirred at 60° C. for 16 hours. After cooling, the reaction mixture was acidified to pH 4 with 1N hydrochloric acid and extracted with ethyl acetate. The organic extract was dried over Na2SO4 and then concentrated in vacuo. Trituration of the oily residue with diethyl ether gave the title compound as a white solid (4.0 g, 91.7%), mp 203° C. (dec.).

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-be62031e91194f7bbb632bfc4d773345
출처 데이터셋
uspto-grants-1994_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05278316

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