Dimethylformamide → HCID 86671822, compound

HRID 2038796Notes

Reaction equation

HRID 2038796 reaction equation
C(C1CCC1(N)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.CN([C:19]([O:23][N:24]1N=NC2C=CC=N[C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CN[O:43][CH3:44].[CH:45](N(C(C)C)CC)([CH3:47])[CH3:46].C[N:55]([CH:57]=[O:58])[CH3:56]>CCOC(C)=O.O>[C:4]([O:3][C:57](=[O:58])[NH:55][C:56]1([C:44](=[O:43])[N:24]([O:23][CH3:19])[CH3:25])[CH2:47][CH2:45][CH2:46]1)([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67516526HCID 67516526, compound

Product 1

HCID 86671822HCID 86671822, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Boc-1-aminocyclobutane-1-carboxylic acid (10.0 g, 45.1 mmol), HATU (20.5 g, 54.1 mmol) and N,O-dimethylhydroxylamine hydrochloride (4.93 g, 49.6 mmol) were combined in DMF (100 mL). To this solution was added diisopropylethylamine (31.4 mL, 180.3 mmol). The reaction was stirred for 2 h, diluted with EtOAc and poured into H2O. The aqueous phase was separated and extracted two more times with EtOAc. The organic layers were combined and washed with brine, dried (Na2SO4), decanted and concentrated in vacuo. The resultant solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane) to afford [1-(methoxy-methyl-carbamoyl)-cyclobutyl]-carbamic acid tert-butyl ester as a white solid (11.5 g, 99%).

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted two more times with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customdecanted
  6. concentrationconcentrated in vacuo
  7. customThe resultant solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane)

Sources & evidence

ORD record
ord-4fb7dd28c12f48f2871c4ddbd9efd407
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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