2,2-Dimethyl-1,3-dioxane-4,6-dione → tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-3-hydroxypropyl)carbamate

HRID 2365047Notes

Reaction equation

HRID 2365047 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].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[C:11]([O:15][C:16](=[O:17])[NH:18][CH2:19][CH2:20][C:21](=[C:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9])[OH:22])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 54704545tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-3-hydroxypropyl)carbamateYield 118.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 2,2-dimethyl-[1,3]dioxane-4,6-dione (7.5 g, 52 mmol), 3-tert-butoxycarbonylamino-propionic acid (9.45 g, 50 mmol), 4-dimethylamino pyridin (9.6 g) in dichloromethane (525 ml) was added dropwise slowly with the solution of N-ethyl-N′-(dimethylaminopropyl)-carbodiimide hydrochloride (11.0 g, 57.5 mmol) in dichloromethane (325 ml). Upon completion of the addition, the mixture was stirred at room temperature overnight, washed with 5% aqueous potassium bisulfate solution (300 ml×4), dried, filtered and concentrated to give [3-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-3-hydroxy-propyl]-carbamic acid tert-butyl ester (18.75 g, 97%) as a light yellow solid.

Workup

  1. additionUpon completion of the addition
  2. washwashed with 5% aqueous potassium bisulfate solution (300 ml×4)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf48e41192ea4cdf838c5e0c474b741b
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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