Aminoacetaldehyde dimethyl acetal → HCID 178495874, compound

HRID 2068529Notes

Reaction equation

HRID 2068529 reaction equation
S=[C:2]1[CH: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]>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:24][O:25][CH:26]([O:29][CH3:30])[CH2:27][NH:28][C:2]1[CH: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

Participants

5

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetal2×HCID 58304049Benzyl N-(2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl)carbamate

Product 1

HCID 178495874HCID 178495874, compoundYield 118%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolve Benzyl N-(2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl)carbamate (1.78 Kg, 5.13 mol) and para-toluene sulfonic acid monohydrate (48.8 g, 256 mmol) in dichloromethane (12 L). Add aminoacetaldehyde dimethyl acetal (2.70 Kg, 25 mole) dropwise over 1 hour and stir for 36 hours at ambient temperature. Add additional aminoacetaldehyde dimethyl acetal (1.40 Kg, 13 mol) and stir for 12 hours at ambient temperature. Add water (5.0 L), separate the organic layer, and extract the aqueous with dichloromethane (2.0 L). Combine the organic layers and wash with water, saturated ammonium chloride (6.0 L), and brine (4.0 L). Filter the organic through diatomaceous earth and concentrate under reduced pressure to give the title compound (2.30 kg, 118%) as a yellow oil: MS (m/z): 398 (M+1).

Workup

  1. stirringstir for 12 hours at ambient temperature
  2. customAdd water (5.0 L), separate the organic layer
  3. extractionextract the aqueous with dichloromethane (2.0 L)
  4. washCombine the organic layers and wash with water, saturated ammonium chloride (6.0 L), and brine (4.0 L)
  5. filtrationFilter the organic through diatomaceous earth
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-9d666702616e4100907991979644d9ed
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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