Hydrochloric Acid → HCID 69423126, compound

HRID 546472Notes

Reaction equation

HRID 546472 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][C@@H:10]1[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24](OC(=O)C)(=[O:26])[CH3:25].Cl.C(OCC)(=O)C>N1C=CC=CC=1>[C:24]([O:15][CH:12]1[CH2:13][CH2:14][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@@H:10]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11]1)(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 68905430HCID 68905430, compound

Product 1

HCID 69423126HCID 69423126, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(1R*,2S*)-N1,N2-Bis(tert-butoxycarbonyl)-4-hydroxy-1,2-cyclohexanediamine (Stereoisomer B) (1.74 g) was dissolved in pyridine (15 ml), and acetic anhydride (5 ml) was added to stir the mixture at room temperature for 4 days. 1N Hydrochloric acid was added to the reaction mixture, extraction was conducted with ethyl acetate, and the resultant organic layer was successively washed with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3) to obtain the title compound (1.96 g) as a colorless oil.

Workup

  1. washthe resultant organic layer was successively washed with 1N hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and then dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-92d61a9fe94f40a2acc91d06e24d76d7
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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