6-tert-Butyl 1-ethyl (E)-(S)-5-[(tert-butoxycarbonyl)amino]-2-(3-fluoropropyl)hex-2-enedioate → HCID 86678429, compound

HRID 1473716Notes

Reaction equation

HRID 1473716 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10]/[CH:11]=[C:12](\[CH2:18][CH2:19][CH2:20][F:21])/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N[C@H](C(OC(C)(C)C)=O)C/C=C(/CCCF)\C(OCC)=O)=O)(C)(C)C>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH2:11][CH:12]([CH2:18][CH2:19][CH2:20][F:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 866784276-tert-Butyl 1-ethyl (E)-(S)-5-[(tert-butoxycarbonyl)amino]-2-(3-fluoropropyl)hex-2-enedioateHCID 866784286-tert-Butyl 1-ethyl (Z)-(S)-5-[(tert-butoxycarbonyl)amino]-2-(3-fluoro-propyl)hex-2-enedioate

Product 1

HCID 86678429HCID 86678429, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-tert-Butyl 1-ethyl (E)-(S)-5-[(tert-butoxycarbonyl)amino]-2-(3-fluoropropyl)hex-2-enedioate and 6-tert-Butyl 1-ethyl (Z)—(S)-5-[(tert-butoxycarbonyl)amino]-2-(3-fluoro-propyl)hex-2-enedioate (100 mg, 0.25 mmol) and palladium (20.0 mg, 10% on charcoal, 0.02 mmol) in ethanol (10 mL) were stirred for 2 h at r.t. under a hydrogen atmosphere. Then the mixture was filtered through Celite® and concentrated under reduced pressure. The crude product was purified by column chromatography (silica, hexanes/ethyl acetate gradient).

Workup

  1. filtrationThen the mixture was filtered through Celite®
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by column chromatography (silica, hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-9ce724dc86cc47d5951f70267ede7582
Source dataset
uspto-grants-2015_04
Patent number
US09017645B2

Reaction notes

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