1,2-Dichloroethane → HCID 86679501, 화합물

HRID 1776545노트

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HRID 1776545 반응식
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[OH:10].[NH2:28][C:29](=[O:51])[CH2:30][N:31]([C:36]1[CH:37]=[C:38]([CH:46]=[CH:47][C:48]=1[O:49][CH3:50])[C:39]([O:41][CH2:42][C:43](O)=[O:44])=[O:40])[S:32]([CH3:35])(=[O:34])=[O:33].C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[NH2:28][C:29](=[O:51])[CH2:30][N:31]([C:36]1[CH:37]=[C:38]([CH:46]=[CH:47][C:48]=1[O:49][CH3:50])[C:39]([O:41][CH2:42][C:43]([O:10][C@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[CH2:8][C:7]1[C:6]([Cl:26])=[CH:5][N+:4]([O-:27])=[CH:3][C:2]=1[Cl:1])=[O:44])=[O:40])[S:32]([CH3:35])(=[O:34])=[O:33]

참가 물질

7

반응물 3

HCID 111,2-DichloroethaneHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 86679500HCID 86679500, 화합물

생성물 1

HCID 86679501HCID 86679501, 화합물수율 36.7%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (30 mg, 0.071 mmol), 2-(3-(N-(2-amino-2-oxoethyl)methylsulfonamido)-4-methoxybenzoyloxy)acetic acid (51.4 mg, 0.143 mmol), DMAP (15 mg, 0.123 mmol), and EDC (100 mg, 0.522 mmol) were dissolved in DMF (2 ml). The reaction was stirred at RT for 3 hours to achieve completion. The reaction mixture was diluted with Water, and the precipitate was washed with water, dissolved in EtOAc and extracted with HCl 1N, Na2CO3 sat. sol. and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum. The crude product was crystallized in EtOH to give (S)-4-(2-(2-(3-(N-(2-amino-2-oxoethyl)methylsulfonamido)-4-methoxybenzoyloxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (20 mg, 0.026 mmol, 36.7% yield).

후처리

  1. washthe precipitate was washed with water
  2. dissolutiondissolved in EtOAc
  3. extractionextracted with HCl 1N, Na2CO3 sat. sol. and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude product was crystallized in EtOH

출처 및 근거

ORD 기록
ord-dfa92840cfb044878fbe3657016bbf3d
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265768B2

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