Triethylamine → HCID 14181424, compound

HRID 1252803Notes

Reaction equation

HRID 1252803 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 mole) and triethylamine (14 ml, 0.1 mole) are dissolved in 200 ml of dichloromethane and stirred in an ice bath while 2-chloroethanesulfonyl chloride (8.2 g, 0.05 mole) 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 is 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. additionis added over 20 minutes
  2. washthe mixture is washed with 5% potassium bisulfate solution, saturated sodium bicarbonate solution and brine
  3. customevaporated in vacuo
  4. customThe semi-solid residue is chromatographed on 350 ml
  5. customis crystallized from ether/hexane, m.p. 84°-87° (7.1 g, 68%)

Sources & evidence

ORD record
ord-ea83a8127ca9467e97dec85ecc8044b6
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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