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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Anisole → HCID 10923331, 화합물

HRID 863653
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인쇄 미리보기

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HRID 863653 반응식
C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:13]([O:16][C@@H:17]1[NH:20][C:19](=[O:21])[C@H:18]1[NH2:22])(=[O:15])[CH3:14].C(N(CC)CC)C.[C:30]1([CH2:36][C:37](Cl)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(OCC)(=O)C.C(OCC)(=O)C.CO>[C:13]([O:16][C@@H:17]1[NH:20][C:19](=[O:21])[C@H:18]1[NH:22][C:37](=[O:38])[CH2:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:15])[CH3:14]
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참가 물질

8

반응물 5

HCID 7519AnisoleHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 6451240Aluminum(III) ChlorideHCID 15428308HCID 15428308, 화합물

생성물 1

HCID 10923331HCID 10923331, 화합물

시약·촉매·용매 2

HCID 8857
Ethyl Acetate
용매
2회
HCID 21584119Ethylacetate methanol용매

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온도
25 °C

실험 절차

To a solution of 0.55 g (2 moles) of (3S,4S)-4-acetoxy-3-benzyl oxycarbonylamino-azetidin-2-one in 2 ml of anisole 0.40 g (3 mmoles) of anhydrous aluminum chloride are added at 20° C., by controlling the reaction by TLC (eluent: ethyl acetate/methanol=95/5 v/v). When the reaction is over, the mixture is filtered off and the filtered solution is concentrated under vacuum to obtain a residue of 0.260 g consisting of crude (3S,4S)-4-acetoxy-3-amino-azetidin-2-one. The residue is taken up with 30 ml of ethyl acetate and to the resulting solution 0.31 g (3 moles) of triethylamine and, afterwards, 0.695 g (4.5 mmoles) of phenylacetyl chloride are added. The mixture is stirred for 6 hours at 20°÷25° C., then it is concentrated under vacuum to obtain a residue which is taken up with ethyl acetate and subjected to a purification on a silica gel column (eluent: ethyl acetate). Thus, 0.165 g of (3S,4S)-4-acetoxy-3-phenylacetamido-azetidin-2-one (II) is obtained.

후처리

  1. filtrationis filtered off
  2. concentrationthe filtered solution is concentrated under vacuum
  3. customto obtain a residue of 0.260 g
  4. concentrationit is concentrated under vacuum
  5. customto obtain a residue which
  6. customsubjected to a purification on a silica gel column (eluent: ethyl acetate)

출처 및 근거

ORD 기록
ord-68fb40761209401bbd85e185466df17d
출처 데이터셋
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05721360

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