HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → Tert-butyl [(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetate

HRID 219983
Notes
Print preview

Reaction equation

HRID 219983 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[CH:19][CH:20]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=3)[CH2:21][O:22][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 59495704(3-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)methanol

Product 1

HCID 86645659Tert-butyl [(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetate

Reagents, catalysts & solvents 2

HCID 94433
Tetrabutylammonium hydrogen sulfate
Catalyst
HCID 1140TolueneSolvent

Procedure

To a solution of (3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)methanol, prepared as in example 159, step 1, (500 mg, 1.29 mmol) in toluene (10 mL) were added tert-butyl bromoacetate (215 μl, 1.45 mmol) and tetrabutylammonium hydrogen sulfate (45 mg, 0.13 mmol), followed by a 33% aqueous solution of sodium hydroxide (10 mL). The biphasic mixture was stirred strongly at RT for 45 minutes. The aqueous layer was removed. The organic layer was diluted with Et2O (20 mL) and washed with water (10 mL), then brine (10 mL). The organic layer was dried (MgSO4) and the solvents were removed under reduced pressure to give a yellow oil. This oil was purified by flash chromatography on silica (cHex/EtOAc) to give the title compound as a colorless oil. LC/MS (Method A): 501.4 (M+H)+. HPLC (Method A) Rt: 6.52 min (purity: 99.5%).

Workup

  1. customThe aqueous layer was removed
  2. additionThe organic layer was diluted with Et2O (20 mL)
  3. washwashed with water (10 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvents were removed under reduced pressure
  6. customto give a yellow oil
  7. customThis oil was purified by flash chromatography on silica (cHex/EtOAc)

Sources & evidence

ORD record
ord-27087d266856426d9cabfebe563e8e3a
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202865B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes