HCID 88542676、化合物 → tert-butyl (S)-1-(4-bromophenyl)ethyl((S)-4-((R)-1,1-dimethylethylsulfinamido)-6-methyl-4-phenylhept-6-enyl)carbamate

HRID 219612ノート

反応式

HRID 219612 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20]/[C:21](=[N:28]\[S@@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[CH3:35][C:36](=[CH2:40])[CH2:37][Mg]Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20][C@@:21]([NH:28][S@@:29]([C:31]([CH3:33])([CH3:32])[CH3:34])=[O:30])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:37][C:36]([CH3:40])=[CH2:35])[C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH3:9])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 88542676HCID 88542676、化合物HCID 178448200HCID 178448200、化合物

生成物 1

HCID 67986476tert-butyl (S)-1-(4-bromophenyl)ethyl((S)-4-((R)-1,1-dimethylethylsulfinamido)-6-methyl-4-phenylhept-6-enyl)carbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of tert-butyl (S)-1-(4-bromophenyl)ethyl((E)-4-((R)-tert-butylsulfinylimino)-4-phenylbutyl)carbamate (1.97 g, 3.59 mmol) in dry THF (60 mL) was cooled to −78° C. A solution of 2-methylallylmagnesium chloride (0.5M in THF, 14.4 mL, 2 equiv) was added slowly. After 2 h, the mixture was warmed to rt and stirred for 1 h. LC-MS found reaction completed. The mixture was quenched with satd aq NH4Cl (10 mL), diluted with ether (100 mL), washed with water (30 mL), brine (25 mL), dried over Na2SO4. Filtration and concentration gave crude tert-butyl (S)-1-(4-bromophenyl)ethyl((S)-4-((R)-1,1-dimethylethylsulfinamido)-6-methyl-4-phenylhept-6-enyl)carbamate (2.30 g) which was used for next steps without further purifications. LC-MS Method 1 tR=2.53 min, m/z 605, 607(M+1).

後処理

  1. customreaction
  2. customThe mixture was quenched with satd aq NH4Cl (10 mL)
  3. additiondiluted with ether (100 mL)
  4. washwashed with water (30 mL), brine (25 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and concentration

出典と根拠

ORDレコード
ord-c8aff95c99b042608a1ab693a9689c76
出典データセット
uspto-grants-2012_06
特許番号
US08202857B2

反応ノート

読み込み中…