Hydrochloric Acid → HCID 9877862, compound

HRID 392643Notes

Reaction equation

HRID 392643 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:18][O:17][C:8]2[CH:9]=[CH:10][C:11]3[NH:12][C:13](=[O:16])[O:14][C:15]=3[C:7]=2[O:6]1)=[N+]=[N-].[H][H].Cl>CO.[Pd]>[NH2:1][CH2:4][CH:5]1[O:6][C:7]2[C:8](=[CH:9][CH:10]=[C:11]3[NH:12][C:13](=[O:16])[O:14][C:15]3=2)[O:17][CH2:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86587693HCID 86587693, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9877862HCID 9877862, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(8S)-8-(Azidomethyl)-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-2(3H)-one (2.86 g, 11.5 mmole) in methanol (60 mL) was treated for 24 hours on a Parr shaker with 60 psi of hydrogen in the presence of 0.43 g of 10% Pd/C and 3.0 mL of 4 N isopropanolic HCl. The catalyst was removed by filtration through celite and was washed with additional methanol. The filtrate was evaporated in vacuum to give 2.12 g (68%) of the (S)-enantiomer of the title compound as a beige solid, m.p.>250° C.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washwas washed with additional methanol
  3. customThe filtrate was evaporated in vacuum

Sources & evidence

ORD record
ord-58087f29a7fd400ca09ba01ad042919e
Source dataset
uspto-grants-2004_10
Patent number
US06800648B2

Reaction notes

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