1,4-Dioxane hydrochloride → HCID 21137721, compound

HRID 1358581Notes

Reaction equation

HRID 1358581 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C@H:4]([CH3:29])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])=[CH:8][C:7]=1[C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.O1CCOCC1>O1CCOCC1>[CH3:1][O:2][C:3](=[O:30])[C@H:4]([CH3:29])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][C:7]=1[C:21](=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 21137722HCID 21137722, compound

Product 1

HCID 21137721HCID 21137721, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-t-butoxycarbonylmethoxy-N-(2-benzoylphenyl)alanine methyl ester (1.4 g), 4N hydrogen chloride/dioxane (10 ml) and dioxane (10 ml) was stirred at room temperature for 3 hours and allowed to stand overnight. The reaction mixture was concentrated under reduced pressure. To the residue was added toluene and the mixture was concentrated under reduced pressure. The residue was chromatographed on a silica gel column (LiChroprepDIOL (Merck)) using hexane: ethyl acetate=2:1−1:1 as the eluant to afford the title compound (0.87 g, Rf=0.53: thin layer chromatography on a silica gel plate using hexane: ethyl acetate=3:2 as the eluant).

Workup

  1. waitto stand overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added toluene
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customThe residue was chromatographed on a silica gel column (LiChroprepDIOL (Merck))

Sources & evidence

ORD record
ord-09c6ccdd961e4b6d9517a89f30f242e2
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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