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Hydrochloric Acid → 5-(4-(2-((Tert-butoxycarbonylamino)methyl)-5-fluorobenzamido)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylic acid

HRID 455315
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HRID 455315 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:11]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][S:19]([N:22]([C:24]1[N:33]=[C:32]([C:34]([O:36]C)=[O:35])[C:31]([O:38][S:39]([C:42]2[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=2)(=[O:41])=[O:40])=[C:30]2[C:25]=1[CH:26]=[CH:27][CH:28]=[N:29]2)[CH3:23])(=[O:21])=[O:20])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+].Cl>O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:11]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][S:19]([N:22]([C:24]1[N:33]=[C:32]([C:34]([OH:36])=[O:35])[C:31]([O:38][S:39]([C:42]2[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=2)(=[O:41])=[O:40])=[C:30]2[C:25]=1[CH:26]=[CH:27][CH:28]=[N:29]2)[CH3:23])(=[O:20])=[O:21])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86667517Methyl 5-(4-(2-((tert-butoxycarbonylamino)methyl)-5-fluorobenzamido)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

생성물 1

HCID 866675185-(4-(2-((Tert-butoxycarbonylamino)methyl)-5-fluorobenzamido)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylic acid
수율 41%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl 5-(4-(2-((tert-butoxycarbonylamino)methyl)-5-fluorobenzamido)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate (Example 3.3; 2.75 mmol) in a 1:1 mixture of THF and water (5.5 mL) was added lithium hydroxide (4.13 mmol) at room temperature. After the reaction was finished, ethyl acetate and water were added. The aquous layer was treated with HCl 1N until pH=5-6. The aqueous layer was extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated, to obtain the target material in 41% yield.

후처리

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customto obtain the target material in 41% yield

출처 및 근거

ORD 기록
ord-d452a700b5fd4662bef4541eda2fe989
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08497270B2

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