Water → HCID 13608674, compound

HRID 1252474Notes

Reaction equation

HRID 1252474 reaction equation
[OH:1][C@H:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=1.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=O.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:13]([C:11]1[S:12][C:8]([CH2:7][CH2:6][CH2:5][N:4]2[CH2:3][C@@H:2]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:1][CH:24]2[C:23]([O:27][CH3:28])=[O:26])=[CH:9][CH:10]=1)([O:15][CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 70205Acetic acid, 2-oxo-, methyl esterHCID 53958894HCID 53958894, compound

Product 1

HCID 13608674HCID 13608674, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.91 g of methyl 5-[3-[[(R)-β-hydroxyphenethyl]amino]propyl]-2-thiophenecarboxylate and 1.05 g of methyl glyoxylate were heated to reflux in 20 ml of toluene for 1 hour on a water separator. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate solutions were dried and evaporated in vacuo. Chromatography of the residue on silica gel gave 1.5 g of methyl(2RS,5R)-3-[3-(5-carbomethoxy-2-thienyl)propyl]-5-phenyl-2-oxazolidinecarboxylate, [α]D =-12° (0.1% in dioxan); ε278 =12300, ε255 =9300.

Workup

  1. washwashed with water
  2. dry with materialThe ethyl acetate solutions were dried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-fa770bc649b546ce997a505647ec9b9b
Source dataset
uspto-grants-1988_05
Patent number
US04743604

Reaction notes

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