2,3-Dihydroxybutanedioic Acid → Ethyl [2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl](hydroxy)acetate

HRID 1881890Notes

Reaction equation

[BH4-].[Na+].C(O)(=O)C(C(C(O)=O)O)O.[O:13]1[CH2:17][CH2:16][O:15][CH:14]1[C:18]1[S:19][C:20]([C:23](=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][N:22]=1>O1CCCC1>[O:15]1[CH2:16][CH2:17][O:13][CH:14]1[C:18]1[S:19][C:20]([CH:23]([OH:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][N:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of sodium borohydride (6.18 g) and DL-tartaric acid (24.5 g) in tetrahydrofuran (250 mL) was stirred at 80° C. for 2 hr. The reaction mixture was cooled to 0° C., ethyl [2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl](oxo)acetate (10.49 g) was added, and the mixture was stirred at room temperature for 2 days. The reaction mixture was slowly poured into ice (100 g), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO9) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (8.43 g, yield 80%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 260 (MH+).

Workup

temperatureThe reaction mixture was cooled to 0° C.
stirringthe mixture was stirred at room temperature for 2 days
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO9)
concentrationconcentrated

Sources & evidence

ORD record: ord-c2844104650542ceadff28de21895c01
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318746B2

Reaction notes

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