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2 protocols using trifluoroborane etherate

1

Flow Synthesis of Poly(glycolic-co-lactic acid)

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l-Lactic acid (≥98%), trifluoroborane etherate, Pd/C (10%), 4-(dimethylamino)pyridine, and N,N′-diisopropylcarbodiimide were purchased from Sigma-Aldrich and used without further purification. Glycolic acid (≥98%) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were purchased from Tokyo Chemical Industry and used without purification. Dichloromethane (DCM) and THF were distilled over CaH2 under N2. Legato 101 syringe pump was purchased from KD Scientific. Cadent 3 syringe pump was purchased from IMI Norgren. SEP-10 was purchased from Zaiput Flow Technologies. Perfluoroalkoxy tubing (1/16″ outside diameter/0.02″ and 0.03″ inside diameter) was purchased from Revodix. Omnifit EZ column was purchased from Diba Industries Inc. Gastorr AG-42-01 was purchased from GL Sciences. CF-2 fraction collector was purchased from Spectrum Chemical Mfg. Corp.
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2

Synthesis of Chiral Organic Compounds

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l-Lactic acid (≥98%), l-mandelic acid (≥99%), allyl bromide, tert-butyldimethylsilyl chloride, trifluoroborane etherate, tetrakis(triphenylphosphine)palladium
(0), and morpholine were purchased from Sigma-Aldrich and used without
further purification. Glycolic acid (≥98%) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide
hydrochloride were purchased from Tokyo Chemical Industry and used
without purification. d-Phenyl lactic acid (≥95%)
was purchased from AK Scientific, Inc. and used without purification.
Dichloromethane was distilled over CaH2 under N2.
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