Diethyl Ether → 2-[(1-Methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester

HRID 874750Notes

Reaction equation

HRID 874750 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[C:15]([OH:17])=O.Cl.[CH3:19][O:20][C:21](=[O:26])[C:22]([NH2:25])([CH3:24])[CH3:23].C(N(CC)C(C)C)(C)C.C(OCC)C>CN(C)C=O.O>[CH3:19][O:20][C:21](=[O:26])[C:22]([NH:25][C:15]([C:6]1[CH:7]=[CH:8][C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[C:5]=1[O:4][CH2:3][O:2][CH3:1])=[O:17])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 688443591-Methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid

Product 1

HCID 688409232-[(1-Methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl esterYield 76.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a round bottom flask was placed 0.96 g 1-methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid, 1.25 g 2-amino-2-methyl-propionic acid methyl ester hydrochloride, 3.09 g of O-(7-azabenzotriazole-1-yl)-N,N,N,N-tetramethyluronium hexafluoro phosphate and 2.83 ml of N,N-diisopropylethylamine in 60 ml of N,N-di-methylformamide. It was left stirring at room temperature overnight. 60 ml of diethylether and 60 ml of water were added to the reaction. The organic layer was separated and washed again with 50 ml of water. It was dried over magnesium sulphate, filtered and concentrated in vacuo to afford a crude yellow oil. Purification was performed by flash chromatography (silica, heptanes/ethyl acetate) to give 1.04 g 2-[(1-methoxymethoxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester.

Workup

  1. customIn a round bottom flask was placed
  2. waitIt was left
  3. customThe organic layer was separated
  4. washwashed again with 50 ml of water
  5. dry with materialIt was dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a crude yellow oil
  9. customPurification

Sources & evidence

ORD record
ord-d74647428f34456e84d44696a4fdb1be
Source dataset
uspto-grants-2015_03
Patent number
US08980938B2

Reaction notes

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