Diisopropylethylamine → (R)-3-tert-Butoxy-2-[(1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid tert-butyl ester

HRID 250305

반응식

HRID 250305 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([OH:15])=O)[N:3]=1.F[P-](F)(F)(F)(F)F.N1([O+]=C(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[C:41]([O:45][C:46](=[O:55])[C@H:47]([NH2:54])[CH2:48][O:49][C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:44])([CH3:43])[CH3:42].C(N(C(C)C)C(C)C)C>ClCCl>[C:41]([O:45][C:46](=[O:55])[C@H:47]([NH:54][C:13]([C:4]1[N:3]=[C:2]([Cl:1])[C:11]2[C:6]([C:5]=1[OH:12])=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:15])[CH2:48][O:49][C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:44])([CH3:42])[CH3:43]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 110205201-Chloro-4-hydroxyisoquinoline-3-carboxylic acidHCID 56777372H-D-Ser(tBu)-OtBu.HClHCID 178484681HCID 178484681, 화합물

생성물 1

HCID 86595447(R)-3-tert-Butoxy-2-[(1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid tert-butyl ester수율 31.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 45 mg (0.2 mmol) of 1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid, 76 mg (0.2 mmol) of benzotriazol-1-yl-(bis-dimethylamino-methylene)-oxonium hexafluoro phosphate (HBTU), 50.8 mg (R)-2-amino-3-tert-butoxy-propionic acid tert-butyl ester hydrochloride (0.2 mmol), and 1 ml of dichloromethane was added 122.5 μl (0.7 mmol) of ethyl-diisopropyl-amine with stirring. Stirring was continued at ambient temperature for 40 h. The product was isolated from the reaction mixture by flash column chromatography on silica gel using hexanes:ethyl acetate (9:1) as the eluent to give a colorless oil. 27 mg of the title compound was obtained; MS-(+)-ion: M+1=422.8 amu.

후처리

  1. stirringStirring
  2. customThe product was isolated from the reaction mixture by flash column chromatography on silica gel
  3. customto give a colorless oil

출처 및 근거

ORD 기록
ord-114dfef9e9f945789a3704cb787d3fe2
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863292B2

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