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

HRID 970812ノート

反応式

HRID 970812 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-6f3333483e3c4592b4f2a5f2c41ae268
出典データセット
uspto-grants-2007_12
特許番号
US07312230B2

反応ノート

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