p-Toluenesulfonic acid → (R)-3-phenyl-2-(5-phenyl-benzoxazol-2-ylmethoxycarbonylamino) Propionic Acid Allyl Ester

HRID 2120603노트

반응식

HRID 2120603 반응식
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([CH2:15][OH:16])=[N:12][C:11]=3[CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19].CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:41]([O:44][C:45](=[O:55])[C@@H:46]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[NH2:47])[CH:42]=[CH2:43].C(N(CC)CC)C>C(Cl)Cl>[CH2:41]([O:44][C:45](=[O:55])[C@H:46]([NH:47][C:18]([O:16][CH2:15][C:13]1[O:14][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:17][C:11]=2[N:12]=1)=[O:19])[CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[CH:42]=[CH2:43]

참가 물질

7

반응물 5

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 11303439(R)-phenylalanine allyl esterHCID 22062842(5-Phenyl-benzoxazol-2-yl)methanol

생성물 1

HCID 12990925(R)-3-phenyl-2-(5-phenyl-benzoxazol-2-ylmethoxycarbonylamino) Propionic Acid Allyl Ester수율 80.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(5-Phenyl-benzoxazole-2-yl)methanol 51 (437 mg, 1.94 mmol) and carbonyldiimidazole (393 mg, 2.43 mmol) in 7 ml of dry CH2Cl2 were stirred at room temperature for 3 hrs. The tosic acid salt of (R)-phenylalanine allyl ester(767 mg, 1.94 mmol) was added followed by 0.42 ml of triethylamine (301 mg, 2.98 mmol). The mixture was stirred overnight. The mixture was diluted and washed with 1M HCl solution then with brine. After drying, the organic phase was filtered and concentrated. The crude product was chromatographed to give about 711 mg of (R)-3-phenyl-2-(5-phenyl-benzoxazol-2-ylmethoxycarbonylamino) propionic acid allyl ester 52.

후처리

  1. additionThe mixture was diluted
  2. washwashed with 1M HCl solution
  3. customAfter drying
  4. filtrationthe organic phase was filtered
  5. concentrationconcentrated
  6. customThe crude product was chromatographed

출처 및 근거

ORD 기록
ord-36fc440f2b8440c2a93eaabac0d6390e
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693098B2

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