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

HRID 2095480Notes

Reaction equation

HRID 2095480 reaction equation
[CH3:1][O:2][C:3](=[O:35])[CH:4]([N:15]1[C:21](=[O:22])[CH2:20][CH2:19][N:18]([C:23](=[O:34])/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:17][CH2:16]1)[CH2:5][CH2:6][O:7][Si](C(C)(C)C)(C)C.Cl>CO>[CH3:1][O:2][C:3](=[O:35])[CH:4]([N:15]1[C:21](=[O:22])[CH2:20][CH2:19][N:18]([C:23](=[O:34])/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:17][CH2:16]1)[CH2:5][CH2:6][OH:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67074257(rac)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-butyric acid methyl ester

Product 1

HCID 67074795(rac)-2-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-4-hydroxy-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.175 g (0.320 mmol) of (rac)-4-(tert-butyl-dimethyl-silanyloxy)-2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-butyric acid methyl ester in 4.9 ml of methanol was treated at 0° C. with 0.8 ml (3.22 mmol, 4 M in dioxane) of HCl and kept 1.5 h at RT. Extraction with cold sat. aq. sodium hydrogencarbonate solution and diethyl ether (2×) followed by drying (Na2SO4) and evaporation gave 0.165 g (quantitative) of the titled compound together with 50% of the lactone (1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-(2-oxo-tetrahydro-furan-3-yl)-[1,4]diazepan-5-one) as a white gum. MS: 429.3 (MH+, 2Cl).

Workup

  1. extractionExtraction with cold sat. aq. sodium hydrogencarbonate solution and diethyl ether (2×)
  2. customby drying
  3. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-af5656a85cf5480c99f22a57bbf0f278
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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