Triethylamine → HCID 178428725, 화합물

HRID 2059937노트

반응식

HRID 2059937 반응식
[OH:1][NH:2][C:3](=[NH:22])[C:4]1[C:5]([CH3:21])=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7]2.C(N(CC)CC)C.[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][C:39]=1[O:40][CH:41]([CH3:43])[CH3:42])[C:34](Cl)=[O:35]>ClCCl>[Cl:30][C:31]1[CH:32]=[C:33]([C:34]([O:1][NH:2][C:3](=[NH:22])[C:4]2[C:5]([CH3:21])=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][N:9]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:8][CH2:7]3)=[O:35])[CH:37]=[CH:38][C:39]=1[O:40][CH:41]([CH3:43])[CH3:42]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 21710470HCID 21710470, 화합물HCID 178428722HCID 178428722, 화합물

생성물 1

HCID 178428725HCID 178428725, 화합물수율 57.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 1,1-dimethylethyl 6-[(hydroxyamino)(imino)methyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 17; 435 mg; 1.42 mmol) in dichloromethane (10 ml) was added triethylamine (0.30 ml; 2.14 mmol) followed by 3-chloro-4-[(1-methylethyl)oxy]benzoyl chloride (Preparation 8; 365 mg; 1.57 mmol) in dichloromethane (5 ml). After 30 min, the reaction was concentrated, and the residue partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous layer was further extracted with ethyl acetate, and the combined organic layers washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with a gradient of 10-50% ethyl acetate in cyclohexane gave the title compound as a white foam (413 mg).

후처리

  1. concentrationthe reaction was concentrated
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate
  3. extractionThe aqueous layer was further extracted with ethyl acetate
  4. washthe combined organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel
  8. washeluting with a gradient of 10-50% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-576851a69f5f452f98218ba6d6bbfd76
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278324B2

반응 노트

불러오는 중…