1,2-Dichloroethane → 3-t-Butoxycarbonylamino-2-(RS)-[(Naphth-2-ylmethyl)-1H-imidazol-5-yl]acetylamino-propionic acid methyl ester

HRID 1292665Notes

Reaction equation

HRID 1292665 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][N:13]1[C:17]([CH2:18][C:19]([OH:21])=O)=[CH:16][N:15]=[CH:14]1.[CH3:22][O:23][C:24](=[O:36])[CH:25]([NH2:35])[CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C1C=C2C(N(O)N=NC2=CC=1)=O.C(N(CC)CC)C.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH3:22][O:23][C:24](=[O:36])[CH:25]([NH:35][C:19](=[O:21])[CH2:18][C:17]1[N:13]([CH2:12][C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:2]=2)[CH:14]=[N:15][CH:16]=1)[CH2:26][NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 3442239Methyl 2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoateHCID 702062051-(2-naphthylmethyl)-1H-imidazol-5-ylacetic acid hydrochloride

Product 1

HCID 675717173-t-Butoxycarbonylamino-2-(RS)-[(Naphth-2-ylmethyl)-1H-imidazol-5-yl]acetylamino-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[1-(Naphth-2-ylmethyl)-1H-imidazol-5-yl]acetic acid hydrochloride (3.83 g, 12.7 mmol), 3-t-butoxycarbonylamino-2(R,S)-aminopropionic acid methyl ester (3.33 g, 15.3 mmol), HOOBT (2.30 g, 14.1 mmol), and triethylamine (5.80 ml, 42.0 mmol) in DMF (150 ml) at 0° C., was added EDC (2.67 g, 13.9 mmol). The reaction was stirred at room temperature for 18 hrs, diluted with EtOAc and the organic layer washed with sat. aq NaHCO3, brine, dried (Na2SO4), and the solvent evaporated in vacuo. The residue was chromatographed (SiO2, 5% MeOH in CH2Cl2) to afford the title compound as a white solid.

Workup

  1. washthe organic layer washed with sat. aq NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customThe residue was chromatographed (SiO2, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5b58df51c8e143489b10689e2826e4c4
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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