Triethylamine → HCID 67219086, compound

HRID 900885Notes

Reaction equation

HRID 900885 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[Cl:12][C:13]1[S:17][C:16]([S:18](Cl)(=[O:20])=[O:19])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23].C(N(CC)CC)C>C1COCC1>[C:7]([O:6][C:5](=[O:11])[NH:4][CH2:3][CH2:2][NH:1][S:18]([C:16]1[S:17][C:13]([Cl:12])=[C:14]([N+:22]([O-:24])=[O:23])[CH:15]=1)(=[O:20])=[O:19])([CH3:8])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 27357835-Chloro-4-nitrothiophene-2-sulfonyl chloride

Product 1

HCID 67219086HCID 67219086, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl N-(2-aminoethyl)-carbamate (0.46 g, 2.87 mmol) in THF (6 ml) was added at 0° C. (ice water bath) 5-chloro-4-nitrothiophene-2-sulfonyl chloride (0.5 g, 1.91 mmol) and triethylamine (0.29 ml, 2.1 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by flash chromatography on silica gel (ethyl acetate/heptane), and subsequent crystallization from ethyl acetate/hexane to yield [2-(5-chloro-4-nitro-thiophene-2-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester (0.53 g, 72%) as a light yellow solid. MS (ISP) 384.1 [(M−H)−], mp 147° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by flash chromatography on silica gel (ethyl acetate/heptane), and subsequent crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-bfdc59b51692428caefcea87c377e2f8
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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