Water → HCID 67090043, compound

HRID 2074467Notes

Reaction equation

HRID 2074467 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@@H:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13].[H-].[Na+].C1(C)C=CC(S(OC[CH2:37][C:38]2[O:42][C:41]([C:43]3[CH:48]=[C:47]([O:49][CH3:50])[C:46]([O:51][CH3:52])=[C:45]([O:53][CH3:54])[CH:44]=3)=[N:40][C:39]=2[CH3:55])(=O)=O)=CC=1.O.[CH3:58]N(C)C=O>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@@H:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:58][CH2:55][C:39]2[N:40]=[C:41]([C:43]3[CH:44]=[C:45]([O:53][CH3:54])[C:46]([O:51][CH3:52])=[C:47]([O:49][CH3:50])[CH:48]=3)[O:42][C:38]=2[CH3:37])=[CH:19][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 59021620HCID 59021620, compoundHCID 86612032HCID 86612032, compound

Product 1

HCID 67090043HCID 67090043, compound

Procedure

To the solution of 3.12 g of methyl (2S)-2-(1,3-benzoxazol-2-ylamino)-3-(4-hydroxyphenyl)propionate in 50 ml of dimethylformamide 60% suspension of NaH in mineral oil (0.4 g) was added portionwise with stirring at room temperature under argon atmosphere. When the evolution of the gas ceased, the solution of 2-[4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-oxazol-5-yl]ethyl 4-toluenesulfonate (4.47 g, 10 mmol) in dimethylformamide was added dropwise. The mixture was heated at 80° C. with stirring. After cooling, the mixture was poured into 1 l of water and extracted several times with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate and the solvent was evaporated, to obtain crude methyl (2S)-2-(1,3-benzoxazol-2-ylamino)-3-[4-(2-[5-methyl-2-(3,4,5-trimethoxy-phenyl)-1,3-oxazol-4-yl]ethoxy)phenyl]propionate.

Workup

  1. additionwas added portionwise
  2. temperatureThe mixture was heated at 80° C.
  3. stirringwith stirring
  4. temperatureAfter cooling
  5. extractionextracted several times with ethyl acetate
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ad25ece096104f4aa9c8204152989616
Source dataset
uspto-grants-2011_04
Patent number
US07919515B2

Reaction notes

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