Hydrochloric Acid → HCID 24997350, compound

HRID 2421502Notes

Reaction equation

HRID 2421502 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:19][CH2:18][C@@:10]3([NH:14]C(=O)N(C)[C:11]3=[O:17])[CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].[O:22]1CCOCC1.Cl>O.C(O)(=O)C>[NH2:14][C@:10]1([C:11]([OH:22])=[O:17])[CH2:18][CH2:19][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 25002107HCID 25002107, compound

Product 1

HCID 24997350HCID 24997350, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a slurry of (5R,7S)-7-(4-bromo-phenyl)-3-methyl-1,3-diaza-spiro[4.4]nonane-2,4-dione (79 g, 0.24 mol) in water (1 L) was added 2 M aqueous NaOH (1 L, 2 mol) and dioxane (200 mL). The resulting mixture was heated to reflux for 24 hours. The reaction mixture was cooled to room temperature, diluted with water (2 L) and acidified with concentrated HCl until a precipitate began to form (about pH 7). Acetic acid (about 20 mL) was added, producing a thick precipitate. The white precipitate was collected and washed with water (2×1 L) and EtOAc (1 L). The filter cake was suspended in toluene (1 L) and concentrated in vacuo at 45° C. This process was repeated once more. The white precipitate was dried to a constant weight under vacuum to give (1R,3S)-1-amino-3-(4-bromo-phenyl)-cyclopentanecarboxylic acid (65 g, 95%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 24 hours
  3. customto form (about pH 7)
  4. customproducing a thick precipitate
  5. customThe white precipitate was collected
  6. washwashed with water (2×1 L) and EtOAc (1 L)
  7. concentrationconcentrated in vacuo at 45° C
  8. customThe white precipitate was dried to a constant weight under vacuum

Sources & evidence

ORD record
ord-a554854179e048f3ba93af9d532d5176
Source dataset
uspto-grants-2011_06
Patent number
US07956195B2

Reaction notes

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