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Diethylamine → Cyclopentyl(2S)-5-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoate

HRID 425030
Notes
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Reaction equation

HRID 425030 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][C:19]#[CH:20])[C:10]([O:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1.C(NCC)C>C(OCC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]#[C:19][CH2:18][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([O:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)=[O:11])=[CH:23][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 115221-Bromo-4-iodobenzeneHCID 59243606cyclopentyl(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoate

Product 1

HCID 59243578Cyclopentyl(2S)-5-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoateYield 75%

Reagents, catalysts & solvents 3

HCID 83717Copper iodide
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of cyclopentyl(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoate (2.45 g, 8.72 mmol) and 4-iodo-bromobenzene (2.96 g, 10.46 mmol) in diethyl ether (4 ml) was added copper iodide (0.166 g, 0.872 mmol) and PdCl2(PPh3)2 (0.306 g, 0.436 mmol). Diethylamine (5.43 ml, 52.3 mmol) was then added and the mixture stirred at RT. After 2 hrs, LCMS showed complete reaction. The mixture was poured onto water and extracted with diethyl ether. The combined organic layers were washed with water and brine, dried over magnesium sulphate, filtered and evaporated in vacuo. The crude residue was subjected to column chromatography eluting with 5 to 10% EtOAc in hexanes. Yield=2.9 g, 6.51 mmol, 75% yield. LCMS purity 98%: m/z 437 [M+H]+.

Workup

  1. customreaction
  2. additionThe mixture was poured onto water
  3. extractionextracted with diethyl ether
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. washeluting with 5 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-d37cb4d08d574798bbb03ca5e2fa5950
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106091B2

Reaction notes

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