Hydroxylamine → HCID 131731595, compound

HRID 404179Notes

Reaction equation

HRID 404179 reaction equation
[OH:1]N.C(OC(=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH:17]=[CH:16][N:15]=1)C.C[N:35]([CH:37]=[O:38])C>CO>[OH:1][NH:35][C:37](=[O:38])[CH:12]([N:13]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH:17]=[CH:16][N:15]=1)[CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 6228DimethylformamideHCID 58545044HCID 58545044, compound

Product 1

HCID 131731595HCID 131731595, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HONH2 (50% aqueous, 2 mL) was added to II (37 mg, 0.09 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 (100:4 to 100:8) to furnish III as a yellow oil (20 mg, 55%).

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 (100:4 to 100:8)

Sources & evidence

ORD record
ord-0ef3e180d5454a7a9daaf887db876478
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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