3,3-Dimethylbutylamine → HCID 90019239, compound

HRID 1052139Notes

Reaction equation

HRID 1052139 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=O)[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][C:18]([CH3:23])([CH3:22])[CH2:19][CH2:20][NH2:21].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14](=[O:16])[NH:21][CH2:20][CH2:19][C:18]([CH3:23])([CH3:22])[CH3:17])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 197093,3-DimethylbutylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11020613(1R,3S,5R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

Product 1

HCID 90019239HCID 90019239, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1R,3S,5R)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester (300 mg, 1.32 mmol), 3,3-dimethyl-butylamine (134 mg, 1.32 mmol) and HBTU (751 mg, 1.98 mmol) in CH2Cl2 (9 mL) under a nitrogen atmosphere was added DIPEA (0.922 mL, 5.28 mmol). The reaction mixture was stirred at RT for 16 h. CH2Cl2 and water were added, the phases were separated and the aqueous layer extracted with CH2Cl2 (×2). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residual material was purified by flash chromatography on silica gel (c-hexane/AcOEt 1-0 to 0-1) to give the title compound. TLC, Rf (EtOAc)=0.85.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous layer extracted with CH2Cl2 (×2)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residual material was purified by flash chromatography on silica gel (c-hexane/AcOEt 1-0 to 0-1)

Sources & evidence

ORD record
ord-49ee5846320343e3a5d655f19abd173c
Source dataset
uspto-grants-2016_07
Patent number
US09388199B2

Reaction notes

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