Dimethylformamide → 4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(s)-thiazolidine-3-carboxylic acid tert-butyl ester

HRID 1791370노트

반응식

HRID 1791370 반응식
CC(OC([CH:8]1[S:12][CH2:11][CH:10]([C:13]([OH:15])=O)[NH:9]1)=O)(C)C.[CH2:16](OC(Cl)=O)[CH:17]([CH3:19])[CH3:18].CN1CC[O:28]CC1.[C:31]([C:33]1[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=1)[C:36]([NH:38]O)=[NH:37])#[N:32].CN([CH:46]=[O:47])C>C1COCC1>[C:17]([O:28][C:46]([N:9]1[C@@H:10]([C:13]2[O:15][N:38]=[C:36]([C:35]3[CH:40]=[CH:41][CH:42]=[C:33]([C:31]#[N:32])[CH:34]=3)[N:37]=2)[CH2:11][S:12][CH2:8]1)=[O:47])([CH3:19])([CH3:18])[CH3:16]

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 79724-Methylmorpholine2회HCID 62365Isobutyl chloroformateHCID 220327532-[(2-Methylpropan-2-yl)oxycarbonyl]-1,3-thiazolidine-4-carboxylic acidHCID 178509779HCID 178509779, 화합물

생성물 1

HCID 696193594-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(s)-thiazolidine-3-carboxylic acid tert-butyl ester수율 20%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
120 °C

실험 절차

4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(S)-thiazolidine-3-carboxylic acid tert-butyl ester (212 mg, 20%, yellow oil) was prepared according to the procedure in Example 25 from Boc-L-thiazolidine-4-carboxylic acid (696 mg, 2.98 mmol) with isobutylchloroformate (0.43 ml, 3.28 mmol) and N-methylmorpholine (0.36 ml, 3.28 mmol) in THF (5 ml) at 40° C. for 2 h. Then 3-cyano-N-hydroxy-benzamidine (577 mg, 3.58 mmol) and additional N-methylmorpholine (0.39 ml, 3.58 mmol) and THF (4 ml) at room temperature overnight followed by extraction of the product and addition of DMF (2 ml) and the mixture was heated at 120° C. overnight. The crude residue was purified on silica gel using 20% ethyl acetate.

후처리

  1. customThe crude residue was purified on silica gel using 20% ethyl acetate

출처 및 근거

ORD 기록
ord-b04a569322c9446191de98fea4a5dc0b
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074809B2

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