Triethylamine → HCID 59191328, compound

HRID 1023990Notes

Reaction equation

HRID 1023990 reaction equation
[CH2:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][C:9]=2[F:17])=[C:5]([OH:20])[CH:4]=1)[CH3:2].[C:21]([NH:28][CH2:29][C:30](O)=[O:31])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C1COCC1>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:18]=[CH:19][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=2[O:20][C:30](=[O:31])[CH2:29][NH:28][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])=[C:9]([F:17])[CH:10]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59191369HCID 59191369, compound

Product 1

HCID 59191328HCID 59191328, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluorophenyl]ethanone (0.37 mmol; 100 mg) in dry THF (2 mL) cooled to 0° C. were added, N-Boc-glycine (0.37 mmol; 64 mg), benzotriazol-1-yloxytris(dimethylamino)phosphoniumhexafluoro phosphate (0.37 mmol; 190 mg) and triethylamine (1.09 mmol; 153 μL). The reaction was stirred at 0° C. for 3 hours and overnight at room temperature. The mixture was concentrated, treated with saturated NH4Cl and extracted with dichloromethane. Combined organic phases were washed with water, dried over Na2SO4 and concentrated in vacuo. The title compound (91 mg; 58%) was obtained as clear oil after purification on preparative TLC (cyclohexane/ethyl acetate: 7/3).

Workup

  1. additionwere added
  2. concentrationThe mixture was concentrated
  3. additiontreated with saturated NH4Cl
  4. extractionextracted with dichloromethane
  5. washCombined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-295aa10c042942f8b6e36490761f8f1a
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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