Water → HCID 117610999, compound

HRID 588900Notes

Reaction equation

HRID 588900 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](I)[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[Cl:11].[NH2:12][C@@H:13]([CH3:17])[C:14]([OH:16])=[O:15].C1(NN=CC2C=CC=CC=2O)C=CC=CC=1.O>CN(C=O)C.[Cu]I.CCOCC>[Br:1][C:2]1[C:3]([Cl:11])=[CH:4][C:5]([O:9][CH3:10])=[C:6]([NH:12][C@@H:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 5950L-AlanineHCID 2498422-Hydroxybenzaldehyde phenylhydrazoneHCID 904557191-Bromo-2-chloro-5-iodo-4-methoxybenzene

Product 1

HCID 117610999HCID 117610999, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-bromo-2-chloro-5-iodo-4-methoxybenzene (3 g, 8.64 mmol), (S)-2-aminopropanoic acid (769 mg, 8.64 mmol), CuI (164 mg, 0.864 mmol), 2-hydroxybenzaldehyde phenylhydrazone (366 mg, 1.73 mmol), K3PO4.3H2O (4.6 g, 17.28 mmol) in DMF (10 mL) was stirred under argon at 80° C. for 16 h. The mixture was allowed to cool to RT, H2O and Et2O were added to the solution. The resulting solution was partitioned into two phases, the aqueous phase was separated, and the organic layer was extracted with 5% NaOH. The combined aqueous phase was acidified to pH 4 with 20% HCl, and then extracted with Et2O. The resulting organic layer was dried over MgSO4 and concentrated in vacuo to afford the desired product (1.7 g, 64% yield). ESI-MS m/z: 306.1[M+H]−

Workup

  1. temperatureto cool to RT
  2. customThe resulting solution was partitioned into two phases
  3. customthe aqueous phase was separated
  4. extractionthe organic layer was extracted with 5% NaOH
  5. extractionextracted with Et2O
  6. dry with materialThe resulting organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c718b8bd3224115866d11c8b2c71dd9
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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