Water → N-Benzyloxycarbonyl-L-threonine phenacyl ester

HRID 1720091노트

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HRID 1720091 반응식
[CH3:1][C@@H:2]([OH:18])[C@H:3]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].O>CC(=O)OCC.C(O)(C)C>[CH2:27]([O:5][C:4](=[O:6])[C@H:3]([C@@H:2]([CH3:1])[OH:18])[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]

참가 물질

7

반응물 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 88217N-((Benzyloxy)carbonyl)-L-threonine

생성물 1

HCID 54036068N-Benzyloxycarbonyl-L-threonine phenacyl ester

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매2회

실험 절차

25.3 g (0.1 mol) of Z-L-threonine were suspended in 200 ml of EA, and 14 ml (0.1 mol) of triethylamine were added. While stirring, 19.0 g (0.1 mol) of solid ω-bromoacetophenone were added in one portion to result initially in a clear solution, which soon became cloudy. The mixture was left to stand for 2 d, diluted with 500 ml of EA and worked up as usual. The crystalline residue was dissolved in 420 ml of hot isopropanol, 300 ml of hot water were added, and the mixture was left to stand in the dark for 2 d. The long white needles which separated out were filtered off, washed and dried in air in the dark. Yield: 27.8 g (0.075 mol, 75%), melting point 129°-130° C., α!D25 =32.2° (c=2.04, EA)

후처리

  1. customto result initially in a clear solution, which soon became cloudy
  2. waitThe mixture was left
  3. waitthe mixture was left
  4. customdark for 2 d
  5. customThe long white needles which separated out
  6. filtrationwere filtered off
  7. washwashed
  8. customdried in air in the dark
  9. customα!D25 =32.2° (c=2.04, EA)

출처 및 근거

ORD 기록
ord-cacd857c655b41bda55651a4371064db
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05504189

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