Citric Acid → N-((1,1-Dimethylethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine

HRID 652748노트

반응식

HRID 652748 반응식
[C:1]([S:20][CH2:21][C@@H:22]([C:24]([OH:26])=[O:25])[NH2:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:29](=O)([O:35]C(C)(C)C)[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[C:29]([NH:23][C@H:22]([C:24]([OH:26])=[O:25])[CH2:21][S:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:35]

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 76044S-Trityl-L-CysteineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

생성물 1

HCID 11167161N-((1,1-Dimethylethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of S-trityl cysteine (see Hiskey and Adams, J. Org. Chem., 30:1340, (1965)) (36.3 g, 0.10 mol) in dioxane (200 ml) and 1M aqueous NaOH (100 ml, 0.10 mol) was added di-t-butyl carbonate (25.36 g, 0.12 mol). The resulting opaque solution became warm and effervesced and the pH fell from 12 to 8 over one hour. After stirring for 90 min, 50% aqueous citric acid (40 ml) was added and the resulting mixture (pH 4) was extracted with ether. The ether was washed with water, then saturated brine, dried (MgSO4), filtered and evaporated to give N-BOC-S-(triphenylmethyl)-cysteine as an oil. Half of this material was dissolved in ether (200 ml) and treated with dicyclohexylamine (10 ml, 50 mmol) to give compound (XX) as a white precipitate which was filtered off, washed with ether and dried (25.1 g, 78%), mp 205°-207°.

후처리

  1. temperatureThe resulting opaque solution became warm
  2. extractionthe resulting mixture (pH 4) was extracted with ether
  3. washThe ether was washed with water
  4. dry with materialsaturated brine, dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-bfc8dd1bf5f64f36a0b33e3d3e8561a7
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04673562

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