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

HRID 351390

反応式

HRID 351390 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-cd281643e9fb442fbd1861930cebe5bc
出典データセット
uspto-grants-2007_02
特許番号
US07183270B2

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