Sodium Hydroxide → HCID 90457105, compound

HRID 625859Notes

Reaction equation

HRID 625859 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH:11]1[C:23]2[CH:22]([CH2:24][O:25][C:26]([NH:28][C@@H:29]([CH2:33][CH2:34][NH2:35])[C:30]([OH:32])=[O:31])=[O:27])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH:20]1[C:21]2[CH:22]([CH2:24][O:25][C:26]([NH:28][C@@H:29]([CH2:33][CH2:34][NH:35][C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[C:30]([OH:32])=[O:31])=[O:27])[C:23]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 78284Cyclopentanecarbonyl chlorideHCID 7019708(2S)-4-Amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid

Product 1

HCID 90457105HCID 90457105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopentanecarbonyl chloride (78 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 materials were 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 (84.1 mg, 33%).

Sources & evidence

ORD record
ord-99b9e33fbf9b474685e474ee5516b703
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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