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

HRID 1243536Notes

Reaction equation

HRID 1243536 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-a4f9a96fb10440aaba336d1d6025829a
Source dataset
uspto-grants-2006_10
Patent number
US07119098B2

Reaction notes

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