Hydroxylamine → HCID 46852761, compound

HRID 404177Notes

Reaction equation

HRID 404177 reaction equation
[OH:1][NH2:2].C([O:5][C:6](=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29](F)=[CH:28][CH:27]=2)[CH:23]=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)C.C[N:35](C=O)C>CO>[OH:1][NH:2][C:6](=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:20]1[CH:25]=[C:24]([C:26]2[CH:27]=[CH:28][C:29]([NH2:35])=[CH:30][CH:31]=2)[CH:23]=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 6228DimethylformamideHCID 58545066HCID 58545066, compound

Product 1

HCID 46852761HCID 46852761, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HONH2 (50% aqueous, 2 mL) was added to III (30 mg, 0.072 mmol) in DMF (0.5 mL) and MeOH (2 mL) at rt. The reaction mixture was stirred for 22 h, after which the solvents were evaporated under reduced pressure. The resulting residue was dissolved and co-evaporated with toluene (2×2 mL) then was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:10) to furnish IV as a yellow oil (7 mg, 24%).

Workup

  1. customafter which the solvents were evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved
  3. customthen was purified by silica gel column chromatography
  4. washeluting with CH2Cl2/MeOH (100:10)

Sources & evidence

ORD record
ord-839a80435c1246eca9d4e7e0ef5c9f37
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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