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

HRID 1843981Notes

Reaction equation

HRID 1843981 reaction equation
CCN=C=NCCCN(C)C.[C:12]([O:16][C:17]([NH:19][CH2:20][CH2:21][C:22]([OH:24])=O)=[O:18])([CH3:15])([CH3:14])[CH3:13].[CH3:25][C:26]1([CH3:34])[O:33][C:31](=[O:32])[CH2:30][C:28](=[O:29])[O:27]1.CO>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:25][C:26]1([CH3:34])[O:33][C:31](=[O:32])[CH:30]([C:22](=[O:24])[CH2:21][CH2:20][NH:19][C:17](=[O:18])[O:16][C:12]([CH3:13])([CH3:14])[CH3:15])[C:28](=[O:29])[O:27]1

Participants

8

Reactant 4

HCID 887MethanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 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)carbamateYield 85.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

EDCI (59.39 g, 310.8 mmol) was added at 0° C. to a stirred solution of 3-(tert-butoxycarbonylamino)propanoic acid (I-59a: 49 g, 258.9 mmol), meldrum's acid (41.05 g, 284.8 mmol) and DMAP (47.4 g, 388.5 mmol) in DCM (490 mL) and the resulting reaction mass was allowed to stir at room temperature overnight. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mass was washed with 5% KHSO4 solution and separated the layers. The organic layer was dried over Na2SO4 and concentrated to afford 70 g of the product (85.8% yield).

Workup

  1. customthe resulting reaction mass
  2. washThe reaction mass was washed with 5% KHSO4 solution
  3. customseparated the layers
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3330c8da210f442587698a9e7150b316
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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