Hydrochloric Acid → HCID 57692438, compound

HRID 1664603Notes

Reaction equation

HRID 1664603 reaction equation
C([N:8]([CH2:37]C1C=CC=CC=1)[C@@H:9]([C@H:20]([CH2:28][CH:29]([OH:36])COS(C)(=O)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([O:12]CC1C=CC=CC=1)=[O:11])C1C=CC=CC=1.Cl>CO.[Pd]>[C:24]([O:23][C:21]([C@H:20]1[CH2:28][CH:29]([OH:36])[CH2:37][NH:8][C@@H:9]1[C:10]([OH:12])=[O:11])=[O:22])([CH3:25])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57692430HCID 57692430, compound

Product 1

HCID 57692438HCID 57692438, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl 4-tert-butyl (2S,3S)-2-(dibenzylamino)-3-{2-hydroxy-3-[(methylsulfonyl)oxy]propyl}succinate from step 1k (5.02 g, 8.2 mmol) in methanol (40 mL) was added Pd-Black and 1M HCl (4 mL) solution. The mixture was hydrogenated under H2 at 50 psi overnight. The catalyst was filtered off and the solution was concentrated to dryness. The residue was dissolved in ethanol and triethyl amine (2 mL) was added. The solution was refluxed for three hours and then concentrated to dryness to provide the crude compound (2S,3S)-3-(tert-butoxycarbonyl)-5-hydroxypiperidine-2-carboxylic acid, the compound was directly used in the next step. MS (ESI): 189.9 (M+H+-t-Bu); 246.0 (M+H+); 268.0 (M+Na+).

Workup

  1. customwas hydrogenated under H2 at 50 psi overnight
  2. filtrationThe catalyst was filtered off
  3. concentrationthe solution was concentrated to dryness
  4. dissolutionThe residue was dissolved in ethanol
  5. additiontriethyl amine (2 mL) was added
  6. temperatureThe solution was refluxed for three hours
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fcc4a4b3571745e1b99bbd979a408bfd
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Reaction notes

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