Ammonium Chloride → Tert-butyl 5-amino-3,3-dimethyl-5-oxopentanoate

HRID 585571Notes

Reaction equation

HRID 585571 reaction equation
[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]([CH3:14])([CH3:13])[CH2:9][C:10](O)=[O:11])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.[N:23]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[Cl-].[NH4+]>CN(C=O)C>[NH2:23][C:10](=[O:11])[CH2:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 156312555-(Tert-butoxy)-3,3-dimethyl-5-oxopentanoic acid

Product 1

HCID 21927924Tert-butyl 5-amino-3,3-dimethyl-5-oxopentanoateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Tert-butoxy-3,3-dimethyl-5-oxopentanoic acid (6 g, 27.8 mmol) was dissolved in DMF (111 mL) and benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (21.68 g, 41.7 mmol), 1-hydroxybenzotriazole (5.6 g, 41.7 mmol), diisopropylethylamine (19.3 mL, 111 mmol) and ammonium chloride (3 g, 55.6 mmol) were added. The mixture was stirred at room temperature for two hours. The DMF was removed under reduced pressure and the residue dissolved in ethyl acetate. The ethyl acetate was washed with 1N KHSO4, saturated sodium bicarbonate, brine, dried (Na2SO4) and concentrated. The residue was again dissolved in ethyl acetate, washed with 0.1N HCl, 0.1N NaOH, H2O, dried (Na2SO4), passed through a pad of silica and concentrated to give 4.9 g (82%) of the desired product. 1H NMR (DMSO-d6) 7.19 (br s, 1H), 6.71 (br s, 1H), 2.23 (s, 2H), 2.08 (s, 2H), 1.4 (s, 9H), 1.02 (s, 6H).

Workup

  1. customThe DMF was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe ethyl acetate was washed with 1N KHSO4, saturated sodium bicarbonate, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. dissolutionThe residue was again dissolved in ethyl acetate
  7. washwashed with 0.1N HCl, 0.1N NaOH, H2O
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e8bca9f807c24725bb001c9ca2d05c4a
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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