1,2-Dichloroethane → tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-oxopropyl)carbamate

HRID 589986Notes

Reaction equation

HRID 589986 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[C:11]([O:15][C:16]([NH:18][CH2:19][CH2:20][C:21](O)=[O:22])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:11]([O:15][C:16](=[O:17])[NH:18][CH2:19][CH2:20][C:21]([CH:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9])=[O:22])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

Product 1

HCID 68556020tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-oxopropyl)carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (3.81 g, 26.4 mmol) in CH2Cl2 (34 mL) at 0° C. was added 3-[(tert-butoxycarbonyl)amino]propanoic acid (5.0 g, 26.4 mmol), DMAP (4.84 g, 39.6 mmol), and EDC (6.08 g, 31.7 mmol). The mixture was stirred at rt for 5 h. The resulting mixture was washed with 10% aq. KHSO4 (4×), dried (Na2SO4) and concentrated to afford the title compound which was used without further purification. LRMS (ESI) m/z 316.1 [(M+H)+; calcd for C14H21NO7: 316].

Workup

  1. washThe resulting mixture was washed with 10% aq. KHSO4 (4×)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ebd841e527b94de584ad1e2ac0b881b3
Source dataset
uspto-grants-2016_01
Patent number
US09233977B2

Reaction notes

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