Tetrahydrofuran → [2-(1H-Indol-3-yl)-2-oxo-ethyl]-carbamic Acid 3-(3-methyl-but-2-enylcarbamoyl)-2-oxo-2,3-dihydro-thiazol-5-yl Ester

HRID 583784Notes

Reaction equation

HRID 583784 reaction equation
[CH3:1][C:2]([CH3:15])=[CH:3][CH2:4][NH:5][C:6]([N:8]1[C:12](=O)[CH2:11][S:10][C:9]1=[O:14])=[O:7].[H-].[Na+].C(OC([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([C:34](=[O:39])[CH2:35][N:36]=[C:37]=[O:38])=[CH:26]1)=O)(C)(C)C.C1C[O:43]CC1>>[CH3:1][C:2]([CH3:15])=[CH:3][CH2:4][NH:5][C:6]([N:8]1[CH:12]=[C:11]([O:43][C:37](=[O:38])[NH:36][CH2:35][C:34]([C:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:25][CH:26]=2)=[O:39])[S:10][C:9]1=[O:14])=[O:7]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 223425403-(3-Methyl-but-2-en-1-yl)aminocarbonyl-2,4-thiazolidinedioneHCID 223425462-(1-Tert-butoxycarbonyl-indol-3-yl)-2-oxo-ethylisocyanate

Product 1

HCID 10127184[2-(1H-Indol-3-yl)-2-oxo-ethyl]-carbamic Acid 3-(3-methyl-but-2-enylcarbamoyl)-2-oxo-2,3-dihydro-thiazol-5-yl Ester

Procedure

To a stirred solution of 3-(3-methyl-but-2-en-1-yl)aminocarbonyl-2,4-thiazolidinedione (0.01 mol), which may be prepared as described in Step (a) above, in a solvent such as, for example, THF is added 1 mol equivalent of a non-nucleophilic base such as described in Step (f) above, preferably sodium hydride, and the mixture is stirred for from 1 minute to about 1 hour. To the mixture is added a solution of 2-(1-tert-butoxycarbonyl-indol-3-yl)-2-oxo-ethylisocyanate (0.01 mol), which may be prepared as described in Step (f) above, in a solvent such as, for example, THF. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of desired product is formed, the mixture is partitioned between ethyl acetate and water, or optionally the mixture is first rotary evaporated, and the residue is so partitioned. The organic layer is washed with 0.01 M hydrochloric acid, water, brine, and dried over sodium sulfate. The mixture is rotary evaporated to give 2-[1-(tert-butoxycarbonyl)-indol-3-yl)-2-oxo-ethyl]carbamic acid, [3-(3-methyl-but-2-en-1-yl)aminocarbonyl-2,3-dihydrothiazol-2-on-5-yl] ester, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

Workup

  1. additionis added 1 mol equivalent of a non-nucleophilic base such
  2. custommay be prepared
  3. customReaction progress

Sources & evidence

ORD record
ord-463bbc25b19f4bf793081c9962c7e8b7
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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