Sodium Hydroxide → HCID 59060807, compound

HRID 47689Notes

Reaction equation

[CH:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:5]=1[O:6][CH2:7][C@@H:8]1[CH2:10][O:9]1)([CH3:3])[CH3:2].[NH2:18][CH2:19][C@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:30]3[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[CH:32][CH:31]=3)[CH:26]=2)[O:21]1.[OH-].[Na+]>C(O)(C)C>[CH:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:5]=1[O:6][CH2:7][C@@H:8]([OH:9])[CH2:10][NH:18][CH2:19][C@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:30]3[CH:31]=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:38][CH:39]=3)[CH:26]=2)[O:21]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Crude (2S)-2-[(2,6-diisopropylphenoxy)methyl]oxirane (Example 17, 0.55 mmol), was diluted in 2 mL of isopropanol (10% water), and treated with methyl 4-[(2R)-2-(aminomethyl)-3,4-dihydro-2H-chromen-6-yl]benzoate (Example 39, 88 mg, 0.26 mmol). This mixture was stirred at 80° C. for 72 hours, then 1N sodium hydroxide (2 mL) was added to the solution at room temperature, and stirred for another 0.5 hour. The product was then purified by preparative HPLC (Gradient 0-70% Acetonitrile/0.1% aq. TFA) to obtain 56.3 mg of product (as a TFA salt) MH+518.3 (free base).

Workup

stirringstirred for another 0.5 hour
customThe product was then purified by preparative HPLC (Gradient 0-70% Acetonitrile/0.1% aq. TFA)

Sources & evidence

ORD record: ord-9cb09c3b0bca45afbb214f948d123fcf
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699860B2

Reaction notes

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