Triethylamine → HCID 58980322, compound

HRID 1180797Notes

Reaction equation

HRID 1180797 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CCN(CC)CC.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[NH:54][C:55](=[O:61])[O:56][C:57]([CH3:59])([CH3:58])[CH3:60])=[O:10])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 8471Triethylamine2×HCID 114704-Acetylbenzoic AcidHCID 25517Ammonium ChlorideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

Product 1

HCID 58980322HCID 58980322, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution at room temperature of 4-acetylbenzoic acid (395 mg, 2.41 mmol) in anhydrous DMF (15 ml) under nitrogen were added Et3N (369 μl, 2.65 mmol) and BOP reagent (1.171 g, 2.65 mmol), respectively. After 30 min, a solution of t-butyl (2-amino-phenyl)-carbamate (551 mg, 2.65 mmol), Et3N (1.01 ml, 7.22 mmol) in anhydrous DMF (5 ml) was added dropwise. After 19 h, the reaction mixture was poured into a saturated aqueous solution of NH4Cl, and diluted with AcOEt. After separation, the organic layer was successively washed with sat NH4Cl, H2O and brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60→50/50) to afford the title compound III (500 mg, 1.41 mmol, 59% yield) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ(ppm): 9.47 (bs, 1H), 8.10–8.00 (m, 4H), 7.91 (d, J=7.9 Hz, 1H), 7.33–7.15 (m, 3H), 6.67 (s, 1H), 2.67 (s, 3H), 1.53 (s, 9H).

Workup

  1. waitAfter 19 h
  2. customAfter separation
  3. washthe organic layer was successively washed with sat NH4Cl, H2O and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60→50/50)

Sources & evidence

ORD record
ord-0c85a320d9c24307af89227363386b7f
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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