Ethyl oxoacetate → HCID 131734765, compound

HRID 1777378Notes

Reaction equation

HRID 1777378 reaction equation
C(OCC)(=O)C=O.N[C@H](C)CO.CC1C=CC(N2N=CC=N2)=C(C=1)C(O)=O.[CH3:28][C@@H:29]1[CH2:33][O:32][CH:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:30]1[C:39](=[O:52])[C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:41]=1[N:47]1[N:51]=[CH:50][CH:49]=[N:48]1>C1(C)C=CC=CC=1>[CH3:28][C@@H:29]1[CH2:33][O:32][C@@H:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:30]1[C:39](=[O:52])[C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:41]=1[N:47]1[N:51]=[CH:50][CH:49]=[N:48]1

Participants

6

Reactant 4

HCID 70211Ethyl oxoacetateHCID 80308(R)-(-)-2-Amino-1-propanolHCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acidHCID 131734766HCID 131734766, compound

Product 1

HCID 131734765HCID 131734765, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By using ethyl glyoxylate (polymer type, a solution of 47% toluene) (2.0 mL, 9.5 mmol), (2R)-2-aminopropan-1-ol (0.73 mL, 9.5 mmol) and 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (1.0 g, 4.9 mmol), the same procedure as in Reference Example 1 was carried out to obtain a diastereomer mixture of ethyl (2RS,4R)-4-methyl-3-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]-1,3-oxazolidine-2-carboxylate. The obtained diastereomer mixture was purified by thin layer chromatography (1 mm, hexane/EtOAc=66/34) to obtain ethyl (2S,4R)-4-methyl-3-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]-1,3-oxazolidine-2-carboxylate (colorless oil). By using the obtained colorless oil as the raw material, the same procedure as in Reference Example 4 was carried out to obtain the title compound (0.041 g) (colorless oil).

Workup

  1. customto obtain
  2. customThe obtained diastereomer mixture was purified by thin layer chromatography (1 mm, hexane/EtOAc=66/34)

Sources & evidence

ORD record
ord-e45cbd7d249d40ffbba1841fe507b183
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

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