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Aminoacetaldehyde dimethyl acetal → HCID 178495875, compound

HRID 2068536
Notes
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Reaction equation

HRID 2068536 reaction equation
S=[C:2]1[C@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6][C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[NH:3]1.[CH3:24][O:25][CH:26]([O:29][CH3:30])[CH2:27][NH2:28]>O1CCCC1.[Hg](Cl)Cl>[CH3:24][O:25][CH:26]([O:29][CH3:30])[CH2:27][NH:28][C:2]1[C@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6][C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 58304042benzyl N-[(3R)-2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate

Product 1

HCID 178495875HCID 178495875, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Combine benzyl N-[(3R)-2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate (8.71 g, 26.68 mmol), mercury dichloride (HgCl2) (9.42 g, 34.69 mmol), and aminoacetaldehyde dimethyl acetal (11.65 mL, 106.73 mmol;) in tetrahydrofuran (250 mL) and heat to 55° C. for 20 minutes. Cool the mixture to ambient temperature and filter it through diatomaceous earth. Wash the cake with THF and ethyl acetate and concentrate the filtrate under reduced pressure. Dissolve the resulting oil in dichloromethane, wash with warm water (4×) and brine, dry over sodium sulfate, and concentrate the organic layer under reduced pressure to give the title compound (9.78 g, 92%) as a solid: MS (m/z): 398 (M+1).

Workup

  1. filtrationfilter it through diatomaceous earth
  2. washWash the cake with THF and ethyl acetate
  3. concentrationconcentrate the filtrate under reduced pressure
  4. dissolutionDissolve the resulting oil in dichloromethane
  5. washwash with warm water (4×) and brine
  6. dry with materialdry over sodium sulfate
  7. concentrationconcentrate the organic layer under reduced pressure

Sources & evidence

ORD record
ord-85d580b8a5f9496299af2737d96084c3
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08299061B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes