Triethylamine → HCID 14181424, compound

HRID 2309039Notes

Reaction equation

HRID 2309039 reaction equation
[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[CH2:21][CH2:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:23]([CH:22]=[CH2:21])(=[O:25])=[O:24])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

HCID 14181424HCID 14181424, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

L-Proline t-butyl ester (6.9 g. 0.04 mol.) and triethylamine (14 ml., 0.1 mol.) are dissolved in 200 ml. of dichloromethane and stirred in an ice bath while 2-chloroethanesulfonyl chloride (8.2 g., 0.05 mol.) in 100 ml. of dichloromethane is added over 20 minutes. After stirring 2 hours, the mixture is washed with 5% potassium bisulfate solution, saturated sodium bicarbonate solution and brine, then evaporated in vacuo. The semi-solid residue in chromatographed on 350 ml. silica gel using 1:1 ethyl acetate/hexane as eluant. The main fraction, comprising N-(vinylsulfonyl)-L-proline t-butyl ester is crystallized from ether/hexane, m.p. 84°-87° (7.1 g., 68%).

Workup

  1. washthe mixture is washed with 5% potassium bisulfate solution, saturated sodium bicarbonate solution and brine
  2. customevaporated in vacuo
  3. customThe semi-solid residue in chromatographed on 350 ml
  4. customis crystallized from ether/hexane, m.p. 84°-87° (7.1 g., 68%)

Sources & evidence

ORD record
ord-bee7e8a47c344cbdbd77464d49b5f64b
Source dataset
uspto-grants-1987_09
Patent number
US04692458

Reaction notes

Loading…