Sodium Hydroxide → HCID 90457348, compound

HRID 625858Notes

Reaction equation

HRID 625858 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25]([NH:27][C@@H:28]([CH2:32][CH2:33][NH2:34])[C:29]([OH:31])=[O:30])=[O:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH:19]1[C:20]2[CH:21]([CH2:23][O:24][C:25]([NH:27][C@@H:28]([CH2:32][CH2:33][NH:34][C:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)=[O:6])[C:29]([OH:31])=[O:30])=[O:26])[C:22]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 78705Cyclobutanecarbonyl chlorideHCID 7019708(2S)-4-Amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid

Product 1

HCID 90457348HCID 90457348, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclobutanecarbonyl chloride (69.7 mg, 0.588 mmol) and NaOH (0.705 mL, 0.705 mmol) were dropped at the same time to a stirred solution of (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-aminobutanoic acid (200 mg, 0.588 mmol) in THF (1.5 mL) and of NaOH (1N, 0.7 mL) at 0° C. The reaction mixture was allowed to stir at rt for 1 h at which time LC-MS showed 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 (92.6 mg, 37%).

Sources & evidence

ORD record
ord-3938de55bf6d4efb81b6ecfa3fcba976
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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