Tert-Butylamine → HCID 66878467, compound

HRID 1878409Notes

Reaction equation

HRID 1878409 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([F:12])[C:3]=1[C:4]([OH:6])=O.[CH3:13][C:14]([NH2:17])([CH3:16])[CH3:15].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(=O)([O-])O.[Na+]>[C:14]([NH:17][C:4](=[O:6])[C:3]1[C:7]([F:12])=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[F:1])([CH3:16])([CH3:15])[CH3:13]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 27741422,6-Difluoro-3-methylbenzoic acid

Product 1

HCID 66878467HCID 66878467, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 2,6-difluoro-3-methylbenzoic acid (8.75 mmol, 1.5 g), 2-methylpropan-2-amine (9.43 mmol, 1 mL, 0.690 g) and triethylamine (28.7 mmol, 4 mL, 2.90 g) in dichloromethane (20 mL) was added 1-propanephosphonic acid cyclic anhydride (13.50 mmol, 8 mL, 8.59 g, 50% solution In ethyl acetate). The reaction was stirred for 2 hours before being diluted with dichloromethane and aqueous sodium hydrogen carbonate. The organic layer was separated, dried and concentrated under vacuum to yield the title compound (1.1 g). MS (ESI) m/z 228.4 [M+H]+

Workup

  1. customThe organic layer was separated
  2. customdried
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-80e18311d8a64c56b69954694f5917ca
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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