Aminoacetaldehyde dimethyl acetal → HCID 178495874、化合物

HRID 2068529ノート

反応式

HRID 2068529 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 178495874HCID 178495874、化合物収率 118%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9d666702616e4100907991979644d9ed
出典データセット
uspto-grants-2012_10
特許番号
US08299061B2

反応ノート

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