Hydrochloric Acid → (R)-methyl 3-amino-2-hydroxypropanoate hydrochloride

HRID 2102215Notes

Reaction equation

HRID 2102215 reaction equation
C[C:2]1(C)[O:6][C@H:5]([CH2:7][NH:8]C(=O)OCC2C=CC=CC=2)[C:4](=[O:19])[O:3]1.[ClH:21].[H][H]>CO.CCOCC.[Pd]>[ClH:21].[NH2:8][CH2:7][C@@H:5]([OH:6])[C:4]([O:3][CH3:2])=[O:19]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 57864461Benzyl [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]methylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86590828(R)-methyl 3-amino-2-hydroxypropanoate hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Benzyl [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]methylcarbamate (7.76 g) prepared by the method described in Step B above was dissolve in methanol (70 mL) with 0.62 g 10% Pd/C. A 1 M HCl in ether solution was added (25 mL). This mixture was hydrogenated using a hydrogen balloon for 22 hours. The reaction mixture was purged with nitrogen, filtered though a pad of Celite, and evaporated under vacuum to give the title compound as a yellowish solid. 1H NMR (CD3OD, 500 MHz) δ 4.45 (dd, J=4 and 8 Hz, 1H), 3.82 (s, 3H), 3.31 (dd, 1H), 3.15 (dd, J=8 and 13 Hz, 1H).

Workup

  1. customfor 22 hours
  2. customThe reaction mixture was purged with nitrogen
  3. filtrationfiltered though a pad of Celite
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-34edc382bd9f4e4b9dc5d4e6f9b17768
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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