Triethylamine → HCID 59191328, compound

HRID 626080Notes

Reaction equation

HRID 626080 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-75a37744e68c4af489b784cd159c7311
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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