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

HRID 219612

반응식

HRID 219612 반응식
[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

참가 물질

4

반응물 2

HCID 88542676HCID 88542676, 화합물HCID 178448200HCID 178448200, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c8aff95c99b042608a1ab693a9689c76
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202857B2

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