Sodium Hydroxide → HCID 86282691, compound

HRID 1424381Notes

Reaction equation

S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[C@@H:11]([CH2:17][N:18]([CH3:40])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:39])[CH2:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:26]=1[CH2:35][C:36](O)=[O:37])[CH2:10]2.[OH-].[Na+]>C1(C)C=CC=CC=1.ClCCl.ClCCl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[C@@H:11]([CH2:17][N:18]([CH3:40])[CH2:19][CH2:20][CH2:21][N:22]1[C:23](=[O:39])[CH2:24][C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:26]=3[CH2:35][C:36]1=[O:37])[CH2:10]2

Participants

Conditions

Temperature: 25 °C

Procedure

Thionyl chloride (1.68 mmol, 1.68 eq) is added to a suspension of {2-[2-({3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]propyl}amino)-2-oxo-ethyl]-4,5-dimethoxyphenyl}acetic acid (500 mg, 1 mmol) in a mixture of toluene/dichloro-methane (15 ml, 66/33) at 60° C. After remaining in contact for 3 hours 30 minutes, 0.5 mmol of thionyl chloride dissolved in 5 mL of dichloromethane is added (0.5 eq). After remaining in contact for 1 hour 30 minutes, the reaction mixture is cooled to 25° C. 1N aqueous sodium hydroxide solution (10 mL) and dichloromethane (10 mL) are added to the mixture. The two phases are separated, and the organic phase is subjected to drying over sodium sulphate and is then dried. 0.38 g of a dark red oil is obtained. The product may be purified by flash chromatography on a silica column (eluant: dichloromethane/methanol 95/5).

Workup

additionis added (0.5 eq)
waitAfter remaining in contact for 1 hour 30 minutes
customThe two phases are separated
dry with materialto drying over sodium sulphate
customis then dried

Sources & evidence

ORD record: ord-8d0bc180c76d472d92c2bec76063ce9c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927708B2

Reaction notes

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