Cesium carbonate → ethyl-2-(1-{2-[(tert.-butoxycarbonyl)-amino]ethyl}-1H-indol-3-yl)-2-oxoacetate

HRID 1472933Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6])[CH3:2].[C:17]([O-:20])([O-])=[O:18].[Cs+].[Cs+]>>[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:11][CH2:10][NH:9][C:17]([O:20][C:7]([CH3:15])([CH3:8])[CH3:5])=[O:18])[CH:8]=1)=[O:6])[CH3:2]

Participants

Reactant 2

HCID 10796Cesium carbonate

HCID 101242Ethyl 3-indolylglyoxylate

Product 1

HCID 67247601ethyl-2-(1-{2-[(tert.-butoxycarbonyl)-amino]ethyl}-1H-indol-3-yl)-2-oxoacetateYield 135.9%

Procedure

The general procedure 1 was then followed using the above product (6.68 mmol, 1.54 g), ethyl-2-(1H-indol-3-yl)-2-oxoacetate (6.68 mmol, 1.45 g) and Cs2CO3 (9.82 mmol, 3.20 g). The purification was achieved by column chromatography (petro-lether:ethylacetate:diethylamine 5:4:1) to yield ethyl-2-(1-{2-[(tert.-butoxycarbonyl)-amino]ethyl}-1H-indol-3-yl)-2-oxoacetate (4.54 mmol, 68%) as white crystals. Mp=114-115° C. IR {tilde over (ν)} [cm−1]=3357; 2977; 1727; 1686; 1638; 1518. EI-MS (m/z)=360 (7.59%; M+•.). 1H NMR (300 MHz, CDCl3) 8.44 (m; 1H; indole-H); 8.34 (s; 1H; indole-H); 7.42 (m; 1H; indole-H); 7.35 (m; 1H; indole-H); 4.63 (bs; 1H; NH); 4.37 (m; 4H; OCH2CH3; indole-CH2); 3.54 (q; 3J=6.2 Hz; 2H; CH2—N); 1.43 (t; 3H; 3J=7.1 Hz; OCH2CH3); 1.43 (s; 9H; C(CH3)3).

Workup

customThe purification

Sources & evidence

ORD record: ord-c3462403b1b248a78c8b5d0681563f2b
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012659B2

Reaction notes

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