2-Hydroxyphenyl hydrogen sulfate → HCID 69666265, compound

HRID 722139Notes

Reaction equation

HRID 722139 reaction equation
[S:1]([O:5][C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8])([OH:4])(=[O:3])=O.[F:13][C:14]1[C:15]2[CH2:16][CH:17]3[CH:26]([NH2:27])[CH:20]([CH2:21][C:22]=2[CH:23]=[CH:24][CH:25]=1)[CH2:19][CH2:18]3>C1COCC1.C(OCC)(=O)C>[OH:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[O:5][S:1](=[O:3])(=[O:4])[NH:27][CH:26]1[CH:20]2[CH2:19][CH2:18][CH:17]1[CH2:16][C:15]1[C:14]([F:13])=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:21]2

Participants

5

Reactant 2

HCID 30838792-Hydroxyphenyl hydrogen sulfateHCID 21882818HCID 21882818, compound

Product 1

HCID 69666265HCID 69666265, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Catechol sulphate (332 mg, 1.93 mmol) was added to an ice-cooled solution of the amine from Step 4 (360 mg, 1.76 mmol) in THF (5 ml). The mixture was allowed to warm to room temperature, stirred for 18 hours, diluted with ethyl acetate and washed with ammonium chloride (aq) followed by brine. The organic phase was dried and evaporated to give a crude oil which was purified by column chromatography on silica gel eluting with 4:1 isohexane-ethyl acetate to give an orange oil 335 mg (51%). 1H NMR (CDCl3, 360 MHz) δ 7.27 (1H, m), 7.21 (1H, m), 7.05 (2H, m), 6.85–7.95 (3H, m), 6.32 (1H, br s), 5.40 (1H, br d, J=7.5 Hz), 4.02 (1H, q, J=6.4 Hz), 3.19–3.25 (1H, dd, J=16.7, 7.6 Hz), 3.04 (1H, d, J=16.3 Hz), 2.70 (1H, m), 2.50–2.61 (3H, m), 1.74 (2H, m), 1.21 (2H, m). m/z 376 (M−H)−

Workup

  1. washwashed with ammonium chloride (aq)
  2. customThe organic phase was dried
  3. customevaporated
  4. customto give a crude oil which
  5. customwas purified by column chromatography on silica gel eluting with 4:1 isohexane-ethyl acetate

Sources & evidence

ORD record
ord-15e82746cdc04f2ab8f65519a7ca7f17
Source dataset
uspto-grants-2006_11
Patent number
US07138400B2

Reaction notes

Loading…