Hydrochloric Acid → (R)-2-(1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid

HRID 63220

반응식

HRID 63220 반응식
[C:1]1(C2SCC(C(O)=O)N=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C2C(=CC(C#N)=CC=2)C=C1.[NH:26]1[C:34]2[C:29](=[CH:30][C:31]([C:35]3[S:36][CH2:37][C@@H:38]([C:40]([OH:42])=[O:41])[N:39]=3)=[CH:32][CH:33]=2)[CH:28]=[CH:27]1.[OH-].[Na+].[S:45](Cl)(Cl)(=[O:47])=[O:46].Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[NH:26]1[C:34]2[C:29](=[CH:30][C:31]([C:35]3[S:36][CH2:37][C@@H:38]([C:40]([OH:42])=[O:41])[N:39]=3)=[CH:32][CH:33]=2)[CH:28]=[CH:27]1.[C:1]1([S:45]([N:26]2[C:34]3[C:29](=[CH:30][C:31]([C:35]4[S:36][CH2:37][C@@H:38]([C:40]([OH:42])=[O:41])[N:39]=4)=[CH:32][CH:33]=3)[CH:28]=[CH:27]2)(=[O:47])=[O:46])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

10

반응물 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 27513Indole-5-carbonitrileHCID 883272-Phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acidHCID 53363877(R)-2-(1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid

생성물 2

HCID 53363877(R)-2-(1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acidHCID 53363878(R)-2-(1-(Phenylsulfonyl)-1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매

실험 절차

(R)-2-(1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid 63a was synthesized using the same method as used for 42a from 1H-indole-5-carbonitrile and used without further purification. To a vigorously stirring solution of 63a (1 mmol) and tetrabutylammonium hydrogen sulfate (0.15 mmol) in toluene (10 mL) at 0° C. was added 50% aqueous sodium hydroxide (10 mL) and sulfonyl chloride (2 mmol). The resultant solution was stirred at RT for 6 h. Then 1N HCl was added to acidify the mixture to pH=2 and extracted with CH2Cl2, the organic layer was separated and dried (MgSO4); then evaporated to dryness to yield 64a, which were used in subsequent steps without further purification.

후처리

  1. customused without further purification
  2. extractionextracted with CH2Cl2
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthen evaporated to dryness

출처 및 근거

ORD 기록
ord-713e8ad0f15e44628077be93e58e6559
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447049B2

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