Sodium Hydroxide → HCID 90457168, compound

HRID 625862Notes

Reaction equation

HRID 625862 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[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]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=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 682422-Furancarbonyl chlorideHCID 7019708(2S)-4-Amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid

Product 1

HCID 90457168HCID 90457168, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Furan-2-carbonyl chloride (77 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 (107 mg, 41%).

Sources & evidence

ORD record
ord-60ecf2a637ce4f63a5d465e38cb79fd2
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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