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Benzoyl chloride → N-hydroxy-7-(naphthalen-2-yl)-7-oxoheptanamide

HRID 1182490
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HRID 1182490 반응식
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]I)C.C(OC(=O)CCCCCCI)C.[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[C:34](Cl)=[O:35].C(Cl)(=O)C1C=CC=CC=1.[NH2:46][OH:47].Cl>C(N(CC)CC)C>[OH:47][NH:46][C:4](=[O:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:34]([C:25]1[CH:26]=[CH:27][C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=1)=[O:35]
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참가 물질

7

반응물 5

HCID 7412Benzoyl chlorideHCID 752462-Naphthoyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 10660673Ethyl 7-iodoheptanoateHCID 10880140Ethyl 6-iodohexanoate

생성물 1

HCID 11129854N-hydroxy-7-(naphthalen-2-yl)-7-oxoheptanamide수율 55%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

Following the procedure described in Example 18, step 1, 2, 3, but substituting respectively ethyl-6-iodohexanoate for ethyl-7-iodoheptanoate and 2-naphthoyl chloride for benzoyl chloride, and then the resulting carboxylic acid was substituted for 37 in Example 14, step 3, using 1.1 equivalent of NH2OH.HCl and triethylamine each, to afford the title compound 111 in 55% yield. 1H NMR (300 MHz, 20% CD3OD in CDCl3): δ 8.47 (s, 1H), 8.05-7.50 (m, 6H), 3.12 (br t, 2H), 2.15 (br t, 2H), 1.82-1.60 (m, 4H), 1.46 (m, 2H). 13C NMR (75 MHz, 20% CD30D in CDCl3): δ 23.59, 25.02, 28.36, 32.33, 38.06, 123.40, 126.56, 127.46, 128.21, 128.29, 129.29, 129.60, 132.25, 133.78, 135.37, 171.04, 201.04.

출처 및 근거

ORD 기록
ord-a8fa1e7c08dd4c7980148b413788da13
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07288567B2

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