Acetic Acid → [4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehyde

HRID 1867352Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10](/[CH:15]=[CH:16]/[C:17]([N:19]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]([CH2:27][C:28](N(OC)C)=[O:29])[CH2:21][CH2:20]2)=[O:18])[CH:11]=[CH:12][C:13]=1[Cl:14].CC(C)=O.C(O)(=O)C.OS([O-])(=O)=O.[K+]>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10](/[CH:15]=[CH:16]/[C:17]([N:19]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]([CH2:27][CH:28]=[O:29])[CH2:21][CH2:20]2)=[O:18])[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

Conditions

Temperature: -30 °C

Procedure

7.92 ml (7.92 mmol) of a LAH-solution (1.0 M in THF) was dropped to a cooled (−30° C.) suspension of 3.28 g (7.92 mmol) of 2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-N-methoxy-N-methyl-acetamide in 260 ml of THF. The reaction was stirred for 5 min at −30° C. and then cooled to −78° C. The reaction was stopped by adding first 12.8 ml (174.24 mmol) of acetone and afterwards 0.9 mL (15.84 mmol) of acetic acid. The reaction was then powered to an aqueous 10% KHSO4 solution and extracted with ether (3×), the organic phase was dried over Na2SO4 evaporated dissolved in toluene and evaporated (3×) to yield 2.12 g (75%) of the title compound as light yellow foam. MS: 355.0 (MH+, 2Cl).

Workup

temperaturea cooled
temperaturecooled to −78° C
extractionextracted with ether (3×)
dry with materialthe organic phase was dried over Na2SO4
customevaporated
dissolutiondissolved in toluene
customevaporated (3×)

Sources & evidence

ORD record: ord-aee5e64afe87435c86761fa4f4016760
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632829B2

Reaction notes

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