Triethylamine → 1-(2-t-Butyloxycarbonylaminoethylthio)-3-chloropropan-2-one

HRID 2085972Notes

Reaction equation

HRID 2085972 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=[O:4].[C:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][SH:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C>O1CCCC1>[C:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][S:17][CH2:5][C:3](=[O:4])[CH2:2][Cl:1])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107931,3-DichloroacetoneHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiol

Product 1

HCID 227267401-(2-t-Butyloxycarbonylaminoethylthio)-3-chloropropan-2-oneYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1,3-dichloroacetone (5.00 g, 39.37 mmol) in tetrahydrofuran (50 mL) were added 2-t-butyloxycarbonylaminoethanethiol (6.98 g, 37.50 mmol) and triethylamine (3.77 g, 37.50 mmol) at 0° C. After 3 hours the reaction mixture was partitioned between ethyl acetate and water. Organic layer was washed with 1 M hydrochloric acid, water, sodium bicatbonate solution and brine. Organic extract was dried over sodium sulfate and concentrated under reduced pressure to afford oily residue of title product (9.40 g). 1H NMR (CDCl3) δ 1.58 (s, 9H), 2.76 (t, J=6, 2H), 3.40 (m, 2H), 3.58 (s, 2H), 4.42 (s, 2H), 5.00 (br s, 1H).

Workup

  1. customAfter 3 hours the reaction mixture was partitioned between ethyl acetate and water
  2. washOrganic layer was washed with 1 M hydrochloric acid, water, sodium
  3. extractionOrganic extract
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e80c45a0980a4761bc9be38e74699dc4
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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