4-Methylmorpholine → tert-butyl (S)-1-((1S*,2R*,4R*)-4-azido-2-(phenylsulfonylmethyl)cyclohexylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate

HRID 351390

반응식

HRID 351390 반응식
FC(F)(F)C(O)=O.[N:8]([C@@H:11]1[CH2:16][CH2:15][C@H:14]([NH2:17])[C@H:13]([CH2:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:12]1)=[N+:9]=[N-:10].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH:55]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[C@H:56]([C:61](O)=[O:62])[CH2:57][CH2:58][S:59][CH3:60].CN1CCOCC1>CN(C=O)C.CCOC(C)=O>[N:8]([C@@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][C:61](=[O:62])[C@@H:56]([NH:55][C:64](=[O:65])[O:66][C:67]([CH3:68])([CH3:69])[CH3:70])[CH2:57][CH2:58][S:59][CH3:60])[C@H:13]([CH2:18][S:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:21])=[O:20])[CH2:12]1)=[N+:9]=[N-:10]

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 89857Boc-L-methionineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 131726281(1S*,2R*,4R*)-4-azido-2-benzenesulfonylmethyl-cyclohexylamine trifluoroacetate

생성물 1

HCID 131726280tert-butyl (S)-1-((1S*,2R*,4R*)-4-azido-2-(phenylsulfonylmethyl)cyclohexylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate수율 84.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

(1S*,2R*,4R*)-4-azido-2-benzenesulfonylmethyl-cyclohexylamine trifluoroacetate (see 37c) (2.5 g, 6.3 mmol) was dissolved in DMF (15 mL) prior to the addition of BOP reagent (3.4 g) and N-Boc-L-Met-OH (1.9 g). After cooling to 0° C., NMM (2.6 mL) was added. The resulting mixture was warmed to rt and was stirred overnight. The solution was diluted with EtOAc, and was washed successively with brine and sat. NaHCO3. The organic phase was dried (MgSO4), filtered, and concentrated. Flash chromatography of the resulting residue gave tert-butyl (S)-1-((1S*,2R*,4R*)-4-azido-2-(phenylsulfonylmethyl)cyclohexylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate (2.8 g) as a mixture of diastereomers. MS found: (M+H)+=526.2.

후처리

  1. temperatureThe resulting mixture was warmed to rt
  2. washwas washed successively with brine and sat. NaHCO3
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cd281643e9fb442fbd1861930cebe5bc
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183270B2

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