Hydrochloric Acid → 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[4-((3RS,4SR)-3,4-dihydroxy-piperidin-1-yl)-butyl]-[1,4]diazepan-5-one hydrochlorid

HRID 1867431Notes

Reaction equation

HRID 1867431 reaction equation
C([Si](C)(C)[O:6][CH:7]1[CH:12]([O:13][Si](C(C)(C)C)(C)C)[CH2:11][CH2:10][N:9]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[C:31](=[O:32])[CH2:30][CH2:29][N:28]([C:33](=[O:44])/[CH:34]=[CH:35]/[C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=3)[CH2:27][CH2:26]2)[CH2:8]1)(C)(C)C.Cl>CO.O1CCOCC1>[ClH:42].[Cl:43][C:38]1[CH:37]=[C:36](/[CH:35]=[CH:34]/[C:33]([N:28]2[CH2:29][CH2:30][C:31](=[O:32])[N:25]([CH2:24][CH2:23][CH2:22][CH2:21][N:9]3[CH2:10][CH2:11][CH:12]([OH:13])[CH:7]([OH:6])[CH2:8]3)[CH2:26][CH2:27]2)=[O:44])[CH:41]=[CH:40][C:39]=1[Cl:42]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 684323104-{4-[(3RS,4SR)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-piperidin-1-yl]-butyl}-1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one

Product 1

HCID 684330291-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[4-((3RS,4SR)-3,4-dihydroxy-piperidin-1-yl)-butyl]-[1,4]diazepan-5-one hydrochloridYield 145.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.100 g (0.14 mmol) of 4-{4-[(3RS,4SR)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-piperidin-1-yl]-butyl}-1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one in 2 mL of MeOH was cooled (0° C.), treated with 0.35 ml (1.40 mmol) of 4M HCl in dioxane and stirred at RT for 2 h. The solution was evaporated, dissolved in toluene and evaporated (2×) to yield 0.053 g (73%) of the title compound as light brown foam. MS: 484.2 (MH+, 2Cl).

Workup

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

Sources & evidence

ORD record
ord-5625f5f58847475491ac0f4815708aac
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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