Aminoacetaldehyde dimethyl acetal → HCID 178495874, 화합물

HRID 2068529노트

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HRID 2068529 반응식
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

참가 물질

5

반응물 2

HCID 89728Aminoacetaldehyde dimethyl acetal2회HCID 58304049Benzyl N-(2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl)carbamate

생성물 1

HCID 178495874HCID 178495874, 화합물수율 118%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9d666702616e4100907991979644d9ed
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299061B2

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