Water → N-(tert-butoxycarbonyl)-O-(3-nitrobiphenyl-2-yl)-L-serine

HRID 1670430Notes

Reaction equation

HRID 1670430 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.Br[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[C:19]=1[O:27][CH2:28][C@@H:29]([C:38]([OH:40])=[O:39])[NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>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].O1CCOCC1>[C:34]([O:33][C:31]([NH:30][C@H:29]([C:38]([OH:40])=[O:39])[CH2:28][O:27][C:19]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:21][CH:22]=[CH:23][C:18]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 67328353O-(2-bromo-6-nitrophenyl)-N-(tert-butoxycarbonyl)-L-serine

Product 1

HCID 67328913N-(tert-butoxycarbonyl)-O-(3-nitrobiphenyl-2-yl)-L-serine

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

331 mg of phenylboronic acid (2.72 mmol), 50.3 mg of 1,1′-bis(diphenylphosphino)ferrocenepalladium chloride (C35H30Cl4FeP2Pd, MW 816.65, 0.025 mmol) and 3.22 g of caesium carbonate (9.87 mmol) are introduced into a 100 mL round-bottomed flask, with stirring and under an argon atmosphere, containing 16 mL of water, 5 mL of dioxane and 1 g of 34 (2.47 mmol). The medium is heated at 100° C., with stirring, for 1 h. The dioxane is concentrated and the aqueous phase is acidified to pH 2-3, extracted twice with 50 ml of AcOEt. The combined organic phases are dried over MgSO4, filtered and evaporated to dryness. The crude product is chromatographed on a silica cartridge (150 g, eluent CH2Cl2/MeOH, in an MeOH gradient: 1 to 5%). 500 mg of expected product 35 (yellow oil) are recovered.

Workup

  1. stirringwith stirring, for 1 h
  2. concentrationThe dioxane is concentrated
  3. extractionextracted twice with 50 ml of AcOEt
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product is chromatographed on a silica cartridge (150 g, eluent CH2Cl2/MeOH
  8. custom500 mg of expected product 35 (yellow oil) are recovered

Sources & evidence

ORD record
ord-bc11571423cb4dd4911ebdfe2f61ff3e
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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