HCID 86674072, compound → HCID 71060167, compound

HRID 576471Notes

Reaction equation

HRID 576471 reaction equation
[OH:1][C:2]1[CH:18]=[C:17]([OH:19])[C:16]([CH2:20][CH2:21][CH2:22][NH:23]C(=O)C(F)(F)F)=[CH:15][C:3]=1[C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])=[O:5]>[OH-].[NH4+]>[NH2:23][CH2:22][CH2:21][CH2:20][C:16]1[C:17]([OH:19])=[CH:18][C:2]([OH:1])=[C:3]([CH:15]=1)[C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])=[O:5]

Participants

3

Reactant 1

HCID 86674072HCID 86674072, compound

Product 1

HCID 71060167HCID 71060167, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

Compound 5 (167 mg, 0.38 mmol) was incubated in concentrated ammonium hydroxide (4.0 ml) for 1.0 hr at 50 degrees C. The resulting solution was evaporated to dryness and the residue was precipitated from methanol-diethyl ether: 96-mg (74% yield). TLC (50/48/2, ethyl acetate/methanol/acetic acid), Rf=0.50; 1H NMR (DMSO-d6) δ 7.78 (1H, m, aromatic-H), 7.43 (2H, m, aromatic-Hs), 7.18 (1H, m, aromatic-H), 6.95 and 6.26 (2H, 2×s, aromatic-Hs), 2.37 (2H, t, J=6.6 Hz, methylene-Hs), 1.68 (2H, m, methylene-Hs). Note—An additional methylene peak (2Hs) is expected to be hidden under the large water peak covering the range 3.8-3.1 ppm.

Workup

  1. customThe resulting solution was evaporated to dryness
  2. customthe residue was precipitated from methanol-diethyl ether

Sources & evidence

ORD record
ord-e3669c7dc3ba4414b1e5c35a62061d53
Source dataset
uspto-grants-2015_05
Patent number
US09040307B2

Reaction notes

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