1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide

HRID 220258Notes

Reaction equation

HRID 220258 reaction equation
[CH3:1][O:2][CH2:3][C:4]([CH2:9][O:10][CH3:11])([CH3:8])[C:5]([OH:7])=O.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:42]([O:44][CH:45]([O:49][CH2:50][CH3:51])[CH2:46][CH2:47][NH2:48])[CH3:43]>C(Cl)Cl.C1COCC1>[CH2:42]([O:44][CH:45]([O:49][CH2:50][CH3:51])[CH2:46][CH2:47][NH:48][C:5](=[O:7])[C:4]([CH2:3][O:2][CH3:1])([CH3:8])[CH2:9][O:10][CH3:11])[CH3:43]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 219119313-Methoxy-2-(methoxymethyl)-2-methylpropanoic acid

Product 1

HCID 86641927N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamideYield 80.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5 g of 3-methoxy-2-methoxymethyl-2-methyl-propionic acid (prepared as in EP609058) were dissolved in 49 mL of DCM and 12 mL of THF. 11.4 mL of DIPEA, 5.84 g of HOBt, 7.07 g of EDCI and 5.45 g of 3,3-diethoxy-propylamine were added sequentially. The mixture was stirred for 23 h at rt, diluted with DCM and washed with sat. NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using heptane/EtOAc from 3/1 to 0/1 as eluant to yield 7.25 g of N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide as a yellowish oil.

Workup

  1. washwashed with sat. NaHCO3
  2. dry with materialThe organic phase was dried over anh. Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude material was purified by CC

Sources & evidence

ORD record
ord-b28a43bedbd74c4284eabf882dbf590a
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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