1,2-Dichloroethane → HCID 86756105, compound

HRID 1274986Notes

Reaction equation

HRID 1274986 reaction equation
[NH2:1][C@H:2]([C:11]([N:13]1[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][CH2:14]1)=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][CH2:35][CH2:36][C:37](O)=[O:38].C(Cl)CCl.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][CH2:35][CH2:36][C:37]([NH:1][C@H:2]([C:11]([N:13]1[CH2:14][CH2:15][CH:16]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:18]1)=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)=[O:38]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 119834723-(pyridin-2-ylamino)propanoic AcidHCID 54385469HCID 54385469, compound

Product 1

HCID 86756105HCID 86756105, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl [(1-tyrosyl-4-piperidinyl)oxy]acetate, Alig, et. al., EP 372486, (1 mmol), N-(2-pyridinyl)-β-alanine, Chowdhary, et. al., Indian J. Chem., 1990, 29A, 280-284, (1 mmol), EDC (1.5 mmol), and DIEA (3 mmol) in DMF (25 mL) is stirred at RT. The mixture is poured into 5% NaHCO3 and extracted with EtOAc. The combined orgainic phase is washed with H2O, dried (MgSO4) and concentrated. The residue is chromatographed (silica gel) to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined orgainic phase is washed with H2O
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed (silica gel)

Sources & evidence

ORD record
ord-0cf83a33119c40c6840117c10f9edcd1
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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