Benzoin → HCID 54104002, 화합물

HRID 380098

반응식

HRID 380098 반응식
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@@H:2]1[C:7]([OH:9])=O.[C:10]1([C:16]([CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)O)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([N:28]=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:10]1([C:16]2[N:28]=[C:7]([C@@H:2]3[NH:1][C:5](=[O:6])[CH2:4][CH2:3]3)[O:9][C:18]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 8400BenzoinHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 439685D-Pyroglutamic acid

생성물 1

HCID 54104002HCID 54104002, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of D-pyroglutamic acid (30 g) in CH2Cl2 (200 ml) were added benzoin (74 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (68 ml) and 4-dimethylaminopyridine (30 g) at room temperature under N2. After being stirred for 12 hours at room temperature, the solvent was evaporated in vacuo, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The obtained compound and ammonium acetate (60 g) were dissolved in acetic acid (500 ml) and the mixture was stirred for 4 hours at 100° C. After the solvent was removed, the residue was partitioned between ethyl acetate and water. The organic layer was washed with water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (5R)-5-(4,5-diphenyloxazol-2-yl)pyrrolidin-2-one (21.2 g).

후처리

  1. customthe solvent was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. dissolutionThe obtained compound and ammonium acetate (60 g) were dissolved in acetic acid (500 ml)
  7. stirringthe mixture was stirred for 4 hours at 100° C
  8. customAfter the solvent was removed
  9. customthe residue was partitioned between ethyl acetate and water
  10. washThe organic layer was washed with water, sat. NaHCO3 and brine
  11. customThe dried solvent was evaporated in vacuo
  12. customthe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-4711f1f8d222417aacbc503ba9706a33
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300344B1

연결된 노트

불러오는 중…