Hydrochloric Acid → HCID 67502477, compound

HRID 1187762Notes

Reaction equation

HRID 1187762 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl.[OH-].[Na+]>C1COCC1>[NH2:8][C@@H:12]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[CH:17][CH:16]=1)[CH2:11][OH:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67501835HCID 67501835, compound

Product 1

HCID 67502477HCID 67502477, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-4-{2-[4-(4-chloro-phenylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (220 mg) in THF (3 ml) in a pressure tube was added HCl solution (2.55 ml, 4 M solution in dioxane). The tube was sealed and the reaction mixture was shaken at 60° C. for 2 hours. The mixture was then cooled to room temperature and poured into 1 M aq. NaOH and extracted with EtOAc. The phases were then separated and the organic phase was dried over sodium sulphate and concentrated in vacuo to afford (S)-2-amino-4-[4-(4-chloro-phenylamino)-phenyl]-butan-1-ol (148 mg, quant.) as a yellow oil which was used in the next step without further purification. MS (ISP): 293.0 ([{37Cl}M+H]+), 291.1 ([{35Cl}M+H]+).

Workup

  1. customThe tube was sealed
  2. temperatureThe mixture was then cooled to room temperature
  3. extractionextracted with EtOAc
  4. customThe phases were then separated
  5. dry with materialthe organic phase was dried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-efd51593d79849dabc9dd905905de9ad
Source dataset
uspto-grants-2014_03
Patent number
US08673950B2

Reaction notes

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