3,4-Dichlorophenyl isocyanate → HCID 67074021, compound

HRID 2095489Notes

Reaction equation

HRID 2095489 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][NH:12][C@@H:11]([CH3:15])[C:10]1=[O:16])([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[C:21]([N:26]=[C:27]=[O:28])[CH:22]=[CH:23][C:24]=1[Cl:25].C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:27](=[O:28])[NH:26][C:21]2[CH:22]=[CH:23][C:24]([Cl:25])=[C:19]([Cl:18])[CH:20]=2)[C@@H:11]([CH3:15])[C:10]1=[O:16])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 76073,4-Dichlorophenyl isocyanateHCID 8471TriethylamineHCID 67074504HCID 67074504, compound

Product 1

HCID 67074021HCID 67074021, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.75 g (3.10 mmol) of 3-((S)-3-methyl-2-oxo-piperazin-1-yl)-propionic acid tert-butyl ester with 0.1HCl in 16 ml of dichloromethane was treated at 0° C. with 0.70 g (3.70 mmol) of 3,4-dichlorophenyl isocyanate and 0.52 ml (3.70 mmol) of triethylamine. After 30 min the reaction was warmed to room temperature and extracted with aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3, 10% NaCl and dried over Na2SO4 to yield after purification by flash silica gel column (EtOAc/n-heptane 1:2 to 3:1) 0.91 g (68%) of the titled compound as white foam. MS: 374.1 (MH+, 2Cl).

Workup

  1. extractionextracted with aqueous 10% KHSO4/EtOAc (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3, 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customto yield
  5. customafter purification by flash silica gel column (EtOAc/n-heptane 1:2 to 3:1) 0.91 g (68%) of the titled compound as white foam

Sources & evidence

ORD record
ord-d83a1a7c1fd0418a98fe56358ba41426
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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