Cyclopentanecarbonyl chloride → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(cyclopentanecarboxamido)propanoic acid

HRID 625856Notes

Reaction equation

HRID 625856 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:9]1[C:21]2[CH:20]([CH2:22][O:23][C:24]([NH:26][C@@H:27]([CH2:31][NH2:32])[C:28]([OH:30])=[O:29])=[O:25])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1>C1COCC1.[OH-].[Na+]>[CH:18]1[C:19]2[CH:20]([CH2:22][O:23][C:24]([NH:26][C@@H:27]([CH2:31][NH:32][C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[C:28]([OH:30])=[O:29])=[O:25])[C:21]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 78284Cyclopentanecarbonyl chlorideHCID 688638Fmoc-Dap-OH

Product 1

HCID 90457906(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(cyclopentanecarboxamido)propanoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

Cyclopentanecarbonyl chloride (81 mg, 0.613 mmol) and NaOH (0.735 mL, 0.735 mmol) were dropped at the same time to a stirred solution of (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-aminopropanoic acid (200 mg, 0.613 mmol) in THF (1.5 mL) and NaOH (1N, 0.8 mL) at 0° C. The reaction mixture was allowed to stir at rt for 1 h at which time LC-MS showed the desired product peak. The reaction solution was acidified with 1N HCl and extracted with EtOAc (60 mL×1). The crude was purified via flash chromatography (ISCO, silica gel, 12 g column; flow rate 30 mL/min, 100% DCM to 20% MeOH/DCM). Fractions containing the desired product were combined and dried via centrifugal evaporation to provide the title compound (142 mg, 54%).

Sources & evidence

ORD record
ord-bda7786a3c294a99952ff5ee0841e608
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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