Triethylamine → HCID 3736492, compound

HRID 1364562Notes

Reaction equation

HRID 1364562 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].Cl.[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH2:18].C(N(CC)CC)C>ClCCl>[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH:18][S:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 3736492HCID 3736492, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-cyano-benzenesulfonyl chloride in dichloromethane (10 mL) was added amino-acetic acid methyl ester hydrochloride (250 mg, 2 mmol) and triethylamine (1.01 g, 10 mmol). The mixture was stirred for 20 min at r.t and was washed with water. The crude was triturated in methanol to give (4-cyano-benzenesulfonylamino)-acetic acid methyl ester (240 mg, 47%). This material was dissolved in NH3 in methanol (30 mL) followed by addition of Raney Ni (3 g). The mixture was hydrogenated under H2 (60 psi, 1 h, r.t) to provide the title compound (1:5, 230 mg).

Workup

  1. washwas washed with water
  2. customThe crude was triturated in methanol

Sources & evidence

ORD record
ord-6f3f169fae064c92a0b291ffc9151be7
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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