Hydrochloric Acid → 2-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-succinic acid 1-methyl ester

HRID 2095483Notes

Reaction equation

HRID 2095483 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH:4]([N:13]1[C:19](=[O:20])[CH2:18][CH2:17][N:16]([C:21](=[O:32])/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[CH2:15][CH2:14]1)[CH2:5][C:6]([O:8]C(C)(C)C)=[O:7].Cl>O1CCOCC1.O>[CH3:1][O:2][C:3](=[O:33])[CH:4]([N:13]1[C:19](=[O:20])[CH2:18][CH2:17][N:16]([C:21](=[O:32])/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[CH2:15][CH2:14]1)[CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 670742532-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-succinic acid 4-tert-butyl ester 1-methyl ester

Product 1

HCID 670740782-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-succinic acid 1-methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 0.30 g (0.60 mmol) of) 2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-succinic acid 4-tert-butyl ester 1-methyl ester in 1.2 ml of dioxane was cooled down to ˜6° C. and 1.50 ml (6.01 mmol) of hydrochloric acid 4M in dioxane, then 1 drop of water were added and stirring was continued overnight at RT. The solution was evaporated, dissolved in acetonitrile and evaporated (2×) to give the titled compound in quant. yield as yellow oil. MS: 441.2 (M−H−, 2Cl).

Workup

  1. customThe solution was evaporated
  2. dissolutiondissolved in acetonitrile
  3. customevaporated (2×)

Sources & evidence

ORD record
ord-56f6416ad5c64f4f84f0d2f2dd49b8a0
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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