Triethylamine → Ethyl 4-[(methylsulfonyl)amino]butanoate

HRID 842751Notes

Reaction equation

HRID 842751 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[NH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].CCN(CC)CC>C1COCC1>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][NH:7][S:2]([CH3:1])(=[O:4])=[O:3])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 126496614-Aminobutyrate ethyl hydrochloride

Product 1

HCID 53959923Ethyl 4-[(methylsulfonyl)amino]butanoateYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (4.10 g, 35.8 mmol) was added to a suspension of ethyl 4-aminobutyrate hydrochloride (6.00 g, 35.8 mmol) and Et3N (10.8 mL, 77.4 mmol) in THF (230 mL). The resulting suspension was stirred at room temperature for 43 h. The reaction mixture was filtered and the filtrate was concentrated. Flash chromatography (1:1 EtOAc:hexanes to EtOAc) afforded the title compound of Step A (7.08 g). 1H NMR (400 MHz, CDCl3) δ 4.51 (s, 1H), 4.12 (q, 2H), 3.18 (q, 2H), 2.94 (s, 3H), 2.40 (t, 2H), 1.85-1.92 (m, 2H), 1.24 (t, 3H); MS 210 (M++1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7303c7beeb86437da7cd6c567b2aeb53
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

Loading…