1-Hydroxybenzotriazole → HCID 86714205, compound

HRID 1484208Notes

Reaction equation

HRID 1484208 reaction equation
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.C([N:13]([CH:16]([CH3:18])[CH3:17])[CH2:14]C)(C)C.[OH:19]N1C2C=CC=CC=2N=N1.NC1C=[CH:34][C:33]([CH:36]([OH:42])[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32]C=1>C1COCC1>[CH:1]1([O:9][C:14]([NH:13][C:16]2[CH:17]=[CH:34][C:33]([CH:36]([OH:42])[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32][CH:18]=2)=[O:19])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12161723HCID 12161723, compoundHCID 12599566HCID 12599566, compound

Product 1

HCID 86714205HCID 86714205, compoundYield 181.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

The PNP-derivative 34 derived from the minor alcohol 31 (300 mg, 1.03 mmol) was dissolved in 10.3 g THF. Diisopropylethylamine (362 mg, 2.80 mmol) was added, followed by 1-hydroxybenzotriazole (75 mg, 0.556 mmol) and ethyl 2-(4-aminophenyl)-2-hydroxyacetate (325 mg, 1.67 mmol, prepared as described in WO 2009109998). The mixture was stirred in the dark at ca. 30° C. for 6 days. The solvent was removed by rotary evaporation and the residue was chromatographed on 21 g silica, using dichloromethane with gradually increasing amounts of TBME as the eluent. The product eluted with ca. 5% TBME. Rotary evaporation of the product fractions afforded minor (E)-ethyl 2-(4-(((cyclooct-2-en-1-yloxy)carbonyl)amino)phenyl)-2-hydroxyacetate (36) as a viscous oil (350 mg, 1.01 mmol, 99%).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customthe residue was chromatographed on 21 g silica
  3. washThe product eluted with ca. 5% TBME
  4. customRotary evaporation of the product fractions

Sources & evidence

ORD record
ord-b1dbfca4a5da4168b1933c0dea2bbf02
Source dataset
uspto-grants-2016_08
Patent number
US09421274B2

Reaction notes

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