3-Aminophenol → HCID 24811214, compound

HRID 1945398Notes

Reaction equation

HRID 1945398 reaction equation
[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=4)=[O:18])=[CH:13][CH:12]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

6

Reactant 4

HCID 115683-AminophenolHCID 81531DiisopropylethylamineHCID 625381PMID26882240-Compound-8HCID 2724699PyBOP

Product 1

HCID 24811214HCID 24811214, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the (4-adamantan-1-yl-phenoxy)-acetic acid (85.9 mg, 0.3 mmol) and 3-amino-phenol (65.5 mg, 0.6 mmol) in DMF (5.0 mL) were added benzotriazol-1-yl-N-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP) (312.2 mg, 0.6 mmol), and N,N-diisopropylethylamine (DIPEA) (0.11 ml, 0.6 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. Purification by silica gel column chromatography (n-Hexane:EtOAc:MeOH=15:3:1) gave 2-(4-Adamantan-1-yl-phenoxy)-N-(3-hydroxyl-phenyl)acetamide as a white solid (67.6 mg, 59.7% yield).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (n-Hexane:EtOAc:MeOH=15:3:1)

Sources & evidence

ORD record
ord-77319a16f75c4ee785a5cf50ce93a4ed
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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