Ammonium Bicarbonate → 2-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amide

HRID 1701072Notes

Reaction equation

HRID 1701072 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:21]1[S:22][C:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:24]([C:26](O)=[O:27])[N:25]=1)[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:36]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[NH4+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:21]1[S:22][C:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:24]([C:26]([NH2:36])=[O:27])[N:25]=1)[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 14013Ammonium BicarbonateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 541039172-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid

Product 1

HCID 543097762-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amideYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-((1R)-1-(tert-Butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid (0.17 g; 0.362 mmol) was dissolved in methylene chloride (8 ml). 1-Hydroxybenzotriazole (0.049 g; 0.362 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.083 g; 0.434 mmol) were added. The reaction mixture was stirred 15 min at room temperature. Ammonium hydrogencarbonate (0.057 g; 0.724 mmol) was added and the reaction mixture was stirred 12 h at room temperature. Methylene chloride (20 ml) was added and the reaction mixture was washed with sodium hydrogencarbonate (10%; 10 ml), sodium hydrogensulfate (5%; 2×10 ml) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (2×15 cm) using ethyl acetate/heptane (1:1) as eluent to afford 0.155 g of 2-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amide.

Workup

  1. stirringthe reaction mixture was stirred 12 h at room temperature
  2. washthe reaction mixture was washed with sodium hydrogencarbonate (10%; 10 ml), sodium hydrogensulfate (5%; 2×10 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customThe solvent was removed in vacuo
  5. customthe residue was chromatographed on silica (2×15 cm)

Sources & evidence

ORD record
ord-b744f281b93040f5a75be2bc09fe48a8
Source dataset
uspto-grants-2002_02
Patent number
US06350767B1

Reaction notes

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