Triethylamine → HCID 87933942, compound

HRID 1789933Notes

Reaction equation

HRID 1789933 reaction equation
C([N:3](CC)CC)C.[CH2:8]([O:10][C:11](=[O:28])[C:12]([CH:14](N)[C:15]1[S:19][C:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:17][CH:16]=1)=[CH2:13])[CH3:9].[C:29]([OH:32])(=[S:31])[CH3:30]>>[CH2:8]([O:10][C:11](=[O:28])[CH:12]([CH2:13][S:31][C:29](=[O:32])[CH3:30])[CH2:14][C:15]1[S:19][C:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:17][C:16]=1[NH2:3])[CH3:9]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 69650259HCID 69650259, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 87933942HCID 87933942, compoundYield 51.6%

Procedure

Triethyl amine (32 μl; 0.23 mmol) was added to a solution of 2-(2-tert-butoxycarbonyl-amino-thiazol-5-ylmethyl)-acrylic acid ethyl ester (67 mg; 0.21 mmol) in thioacetic acid (0.4 mL) at 0° C. The reaction mixture was stirred at room temperature for 48 hours, and then poured onto ice-water. The aqueous layer was extracted with CH2Cl2. The combined organic phases were washed with saturated NaHCO3, dried and concentrated to yield 190 mg of the crude product. The crude product was purified by flash chromatography (Heptane/EtOAc: 1:0→68:32) to yield 2-acetylsulfanylmethyl-3-(2-tert-butoxycarbonyl-amino-thiazol-5-yl)-propionic acid ethyl ester (43 mg, 51.6%).

Workup

  1. additionpoured onto ice-water
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washThe combined organic phases were washed with saturated NaHCO3
  4. customdried
  5. concentrationconcentrated
  6. customto yield 190 mg of the crude product
  7. customThe crude product was purified by flash chromatography (Heptane/EtOAc: 1:0→68:32)

Sources & evidence

ORD record
ord-2f5983c35a314e8b8afc593cf555a77b
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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