Diisopropylethylamine → HCID 68055604, compound

HRID 1803822Notes

Reaction equation

HRID 1803822 reaction equation
[N:1]([CH2:4][C:5](=[O:28])[NH:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N+:2]=[N-:3].[CH2:29]([O:32][C:33]1[CH:45]=[CH:44][C:36]2[N:37]=[C:38]([S:40]([NH2:43])(=[O:42])=[O:41])[S:39][C:35]=2[CH:34]=1)[C:30]#[CH:31].CCN(C(C)C)C(C)C>[Cu]I.C1COCC1>[O:28]=[C:5]([NH:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:4][N:1]1[CH:31]=[C:30]([CH2:29][O:32][C:33]2[CH:45]=[CH:44][C:36]3[N:37]=[C:38]([S:40](=[O:42])(=[O:41])[NH2:43])[S:39][C:35]=3[CH:34]=2)[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 57446112HCID 57446112, compoundHCID 57446126HCID 57446126, compound

Product 1

HCID 68055604HCID 68055604, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 25 mL round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet containing tert-butyl 1-azido-2-oxo-7,10,13-trioxa-3-azahexadecan-16-ylcarbamate (130 mg, 0.36 mmol), 6-(prop-2-ynyloxy)benzo[d]thiazole-2-sulfonamide (Alkyne, 107 mg, 0.4 mmol), CuI (6.9 mg, 0.036 mmol), and THF (3 mL) was added DIPEA (52 mg, 0.4 mmol). The mixture was stirred at rt for 15 h and concentrated. The crude material was purified with silical chromatography (gradient 10% to 90% EtOAc in hexane) to afford compound 142 as a clear wax (125 mg, 52%). MS (ESI) m/z 694(M+Na+).

Workup

  1. customTo a 25 mL round bottomed flask equipped with a magnetic stir bar
  2. concentrationconcentrated
  3. customThe crude material was purified with silical chromatography (gradient 10% to 90% EtOAc in hexane)

Sources & evidence

ORD record
ord-a914b746faec41729923a45ecc9b81c4
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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