1-Hydroxybenzotriazole → N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide

HRID 2090566Notes

Reaction equation

HRID 2090566 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.[CH2:31]([O:33][CH:34]([O:38][CH2:39][CH3:40])[CH2:35][CH2:36][NH2:37])[CH3:32]>C(Cl)Cl.C1COCC1.C(Cl)CCl>[CH2:31]([O:33][CH:34]([O:38][CH2:39][CH3:40])[CH2:35][CH2:36][NH:37][C:5](=[O:7])[C:4]([CH2:3][O:2][CH3:1])([CH3:8])[CH2:9][O:10][CH3:11])[CH3:32]

Participants

8

Reactant 4

HCID 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 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5 g of 3-methoxy-2-methoxymethyl-2-methyl-propionic acid (prepared as described 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 EDC 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 Hept/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-e3183eda780f473aa91094352e5fc363
Source dataset
uspto-grants-2013_05
Patent number
US08436205B2

Reaction notes

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