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Sodium Carbonate → HCID 69069158, compound

HRID 491150
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Reaction equation

HRID 491150 reaction equation
[CH3:1]OB(O)O.C([O-])([O-])=O.[Na+].[Na+].[NH2:12][C:13]1[C:45]([Cl:46])=[CH:44][C:16]([CH2:17][C@@H:18]([CH2:23][C:24](=[O:43])[N:25]2[CH2:30][CH2:29][CH:28]([N:31]3[CH2:37][CH2:36][C:35]4[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=4[NH:33][C:32]3=[O:42])[CH2:27][CH2:26]2)[C:19]([O:21][CH3:22])=[O:20])=[CH:15][C:14]=1Br>O1CCOCC1.CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:12][C:13]1[C:14]([CH3:1])=[CH:15][C:16]([CH2:17][C@@H:18]([CH2:23][C:24](=[O:43])[N:25]2[CH2:30][CH2:29][CH:28]([N:31]3[CH2:37][CH2:36][C:35]4[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=4[NH:33][C:32]3=[O:42])[CH2:27][CH2:26]2)[C:19]([O:21][CH3:22])=[O:20])=[CH:44][C:45]=1[Cl:46]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 14178740MethylboratHCID 69064064HCID 69064064, compound

Product 1

HCID 69069158HCID 69069158, compound

Reagents, catalysts & solvents 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 887
Methanol
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

Under a nitrogen atmosphere 0.99 g (16.0 mmol) methylboric acid, 15.5 mL 2 M Na2CO3 solution and 1.02 g (1.40 mmol) Pd(dppf)Cl2 were added to a solution of 8.40 g (14.5 mmol) methyl(S)-2-(4-amino-3-bromo-5-chloro-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butanoate in 50 mL 1,4-dioxane and 3 mL MeOH and the reaction mixture was refluxed overnight. The reaction solution was filtered while hot and the filtrate was combined with EtOAc. The organic phase was washed several times with semisaturated NaHCO3 solution and dried over Na2SO4. It was filtered through activated charcoal and evaporated down i.vac. The residue was taken up in a little DCM and purified by chromatography (silica gel, gradient DCM to DCM/MeOH/NH3 90:10:1). The fractions containing the product were combined, evaporated down i.vac., triturated with DIPE, suction filtered and dried.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. filtrationThe reaction solution was filtered while hot and the filtrate
  3. washThe organic phase was washed several times with semisaturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationIt was filtered through activated charcoal
  6. customevaporated down i.vac
  7. custompurified by chromatography (silica gel, gradient DCM to DCM/MeOH/NH3 90:10:1)
  8. additionThe fractions containing the product
  9. customevaporated down i.vac
  10. custom, triturated with DIPE, suction
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-b929a4a669bc4c119e4d88c0df1fddac
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528129B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes