Thionyl Chloride → (2S)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-thiophene-2-carbonyl)-amino)-propionic Acid Isobutyl Ester

HRID 413223Notes

Reaction equation

HRID 413223 reaction equation
[C:1]12([CH2:11][O:12][C:13]([NH:15][C@@H:16]([CH2:20][NH:21][C:22]([C:24]3[S:25][C:26]([CH2:29][CH2:30][C:31](=[O:39])[NH:32][C:33]4[NH:34][CH2:35][CH2:36][CH2:37][N:38]=4)=[CH:27][CH:28]=3)=[O:23])[C:17]([OH:19])=[O:18])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(Cl)(Cl)=O>C(O)C(C)C>[CH2:2]([O:18][C:17](=[O:19])[C@@H:16]([NH:15][C:13]([O:12][CH2:11][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:14])[CH2:20][NH:21][C:22]([C:24]1[S:25][C:26]([CH2:29][CH2:30][C:31](=[O:39])[NH:32][C:33]2[NH:34][CH2:35][CH2:36][CH2:37][N:38]=2)=[CH:27][CH:28]=1)=[O:23])[CH:1]([CH3:10])[CH3:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10415384(S)-2-(Adamantan-1-ylmethoxycarbonylamino)-3-{[5-(3-guanidino-3-oxo-propyl)-thiophene-2-carbonyl]-amino}-propionic acid

Product 1

HCID 15859417(2S)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-thiophene-2-carbonyl)-amino)-propionic Acid Isobutyl EsterYield 139.2%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

0.38 g (0.7 mmol) of (2S)-2-(1-adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid (example 15) were dissolved in 7 ml of isobutanol. Under an inert gas atmosphere and under external ice cooling 0.19 ml of thionyl chloride were cautiously added. After stirring for 8 hours at room temperature the reaction was complete. The solvents were removed in vacuo to give a colourless foam which was purified by chromatography (silica gel; isopropanol/ethyl acetate/water (4/3/1; v/v/v)). The fractions containing the title compound were lyophilized to give 0.30 g of a colourless solid.

Workup

  1. customThe solvents were removed in vacuo
  2. customto give a colourless foam which
  3. customwas purified by chromatography (silica gel; isopropanol/ethyl acetate/water (4/3/1; v/v/v))
  4. additionThe fractions containing the title compound

Sources & evidence

ORD record
ord-e6f92bbf569d4954a5b8495d87e9ad5a
Source dataset
uspto-grants-2003_05
Patent number
US06566366B1

Reaction notes

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