Acetic acid, 2-oxo-, methyl ester → HCID 22838051, compound

HRID 2350928Notes

Reaction equation

HRID 2350928 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C@H:15]([NH:17][CH2:18][CH:19]([OH:28])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:16])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4].[C:29]([O:33][CH3:34])(=[O:32])[CH:30]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.CO.CCOCC>[CH2:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C@H:15]([N:17]2[CH2:18][CH:19]([CH2:20][O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:28][CH:30]2[C:29]([O:33][CH3:34])=[O:32])[CH3:16])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 70205Acetic acid, 2-oxo-, methyl esterHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 54221901HCID 54221901, compound

Product 1

HCID 22838051HCID 22838051, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

387 mg of (RS)-1-[[(R)-3-[α-(butylamino)-p-tolyl]-1-methylpropyl]amino]-3-phenoxy-2-propanol, 102 mg of methyl glyoxylate and 195 mg of p-toluenesulfonic acid monohydrate in 5 ml of benzene were stirred at 20°-25° C. for 6 hours. The mixture was worked up with ether and sodium bicarbonate solution. Chromatography of the crude product on silica gel with ether-methanol gave methyl(2RS,5RS)-3-[(R)-3-[α-(butylamino)-p-tolyl]-1-methylpropyl]-5-phenoxymethyl-2-oxazolidinecarboxylate, [α]D =-9° (c=0.1 in methanol); ε219 =18140, ε270 =1830, ε277 =1430.

Sources & evidence

ORD record
ord-e9cb76b886374278af47bf95934213dc
Source dataset
uspto-grants-1989_10
Patent number
US04871755

Reaction notes

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