Ammonia → HCID 15949135, compound

HRID 910886Notes

Reaction equation

HRID 910886 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13](O)=[O:14])[CH:9]=[CH:10][CH:11]=1.F[P-](F)(F)(F)(F)F.[N:28]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.N>CN(C=O)C>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([NH2:28])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 9838311HCID 9838311, compound

Product 1

HCID 15949135HCID 15949135, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-(2,6-Dimethylbenzyloxy)phenylacetic acid (3.08 g, 11.4 mmol) and Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (5.05 g, 11.4 mmol) in DMF (75 ml) was added triethylamine (2.30 g, 22.8 mmol), and the reaction mixture was stirred for 1 h at room temperature. To this reaction mixture was added liquid ammonia (100 ml) at −40 0° C., the resulting mixture was allowed to warm to ambient temperature over 10-12 hours and concentrated. The residue was taken into ethyl acetate and washed with water (2×), dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (ethyl acetate:hexane, 2.5:1 spiked with acetic acid) to give the title compound.

Workup

  1. temperatureto warm to ambient temperature over 10-12 hours
  2. concentrationconcentrated
  3. washwashed with water (2×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography on a silica gel column (ethyl acetate:hexane, 2.5:1 spiked with acetic acid)

Sources & evidence

ORD record
ord-346db2ead97a47fdbe235640ebcf0ed8
Source dataset
uspto-grants-2011_09
Patent number
US08022249B2

Reaction notes

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