Benzoyl chloride → HCID 90457037, compound

HRID 625861Notes

Reaction equation

HRID 625861 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH:12]1[C:24]2[CH:23]([CH2:25][O:26][C:27]([NH:29][C@@H:30]([CH2:34][CH2:35][NH2:36])[C:31]([OH:33])=[O:32])=[O:28])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH:21]1[C:22]2[CH:23]([CH2:25][O:26][C:27]([NH:29][C@@H:30]([CH2:34][CH2:35][NH:36][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:31]([OH:33])=[O:32])=[O:28])[C:24]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide2×HCID 7019708(2S)-4-Amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid

Product 1

HCID 90457037HCID 90457037, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl chloride (83 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 (160 mg, 57%).

Sources & evidence

ORD record
ord-3e6909a160674c94b01e278dca5fcf1f
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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