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

HRID 1827991Notes

Reaction equation

HRID 1827991 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Phenyl-benzoxazole-2-yl)methanol 51 (437 mg, 1.94mmol) and carbonyidiimidazole (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.

Workup

  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

Sources & evidence

ORD record
ord-8f653813ca2e4888827eab908d74f8b8
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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