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

HRID 219612Notes

Reaction equation

HRID 219612 reaction equation
[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

Participants

4

Reactant 2

HCID 88542676HCID 88542676, compoundHCID 178448200HCID 178448200, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c8aff95c99b042608a1ab693a9689c76
Source dataset
uspto-grants-2012_06
Patent number
US08202857B2

Reaction notes

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