(S)-tert-butyl 3-((R)-2-(pent-4-enoyloxy)-2-phenylethylcarbamoyl)hex-5-enoate → HCID 58348121, compound

HRID 41072

Reaction equation

HRID 41072 reaction equation
[C:1]([O:7][C@H:8]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:9][NH:10][C:11]([C@@H:13]([CH2:22][CH:23]=[CH2:24])[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:12])(=[O:6])[CH2:2][CH2:3]C=C>C1(C)C=CC=CC=1.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.C(Cl)Cl>[O:12]=[C:11]1[C@H:13]([CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:22][CH:23]=[CH:24][CH2:3][CH2:2][C:1](=[O:6])[O:7][C@H:8]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:9][NH:10]1

Participants

5

Reactant 1

HCID 67310751(S)-tert-butyl 3-((R)-2-(pent-4-enoyloxy)-2-phenylethylcarbamoyl)hex-5-enoate

Product 1

HCID 58348121HCID 58348121, compoundYield 73.1%

Reagents, catalysts & solvents 3

HCID 178425456HCID 178425456, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (S)-tert-butyl 3-((R)-2-(pent-4-enoyloxy)-2-phenylethylcarbamoyl)hex-5-enoate (470 mg, 1.13 mmol) in toluene (113 mL) was added Grubbs 2nd Generation catalyst (96 mg, 0.113 mmol) and the reaction mixture was heated to 65° C. Upon stirring 7 h with continued heating, TLC analysis indicated complete consumption of starting material. The reaction mixture was cooled to rt, diluted with degassed CH2Cl2 (11 ml) and Pb(OAc)4 (251 mg, 0.566 mmol) was added. The resulting mixture was stirred for 12 h at which point the mixture was passed through a short plug of silica then concentrated using rotary evaporation. The resulting purple solid was triturated with methanol to further remove ruthenium complexes. The off white solid that remained was purified using silica gel chromatography (MeOH/CH2Cl2 gradient) to yield 320 mg of desired product as a white solid in 73% yield. LRMS (M+Na)+: 410.4.

Workup

  1. customconsumption of starting material
  2. temperatureThe reaction mixture was cooled to rt
  3. additionwas added
  4. stirringThe resulting mixture was stirred for 12 h at which point the mixture
  5. concentrationthen concentrated
  6. customevaporation
  7. customThe resulting purple solid was triturated with methanol to further remove ruthenium complexes
  8. customThe off white solid that remained was purified

Sources & evidence

ORD record
ord-50a922f66a094ce8839cea4ea75ace99
Source dataset
uspto-grants-2013_09
Patent number
US08530456B2

Linked notes

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