Hydrochloric Acid → HCID 59118223, compound

HRID 896880Notes

Reaction equation

C(OC([N:8]([CH2:18][C@H:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([S:29]([C:32]3[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=3)[C:35]([O:37]C)=[O:36])(=[O:31])=[O:30])[CH:25]=2)[O:20]1)[CH2:9][C@H:10]([OH:17])[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=O)(C)(C)C.Cl>O1CCOCC1>[OH:17][C@H:10]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][NH:8][CH2:18][C@H:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([S:29]([C:32]3[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=3)[C:35]([OH:37])=[O:36])(=[O:31])=[O:30])[CH:25]=2)[O:20]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 66.3 mg (0.11 mmol) methyl 3-{[(2R)-2-({(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]sulfonyl}benzoate (Example 176) diluted in 5 mL 1,4-dioxane, was slowly added 0.05 mL of 6N hydrochloric acid. The resulting mixture was then stirred at 45° C. for 2 hours. The crude mixture was concentrated in vacuo, then purified by preparative HPLC. The purified intermediate product was then treated with 0.8 mL of 2N sodium hydroxide and allowed to stir for 36 hours and then concentrated in vacuo. The crude product was then purified by preparative HPLC (0-70% Acetonitrile/0.1% aq TFA) to obtain 6.5 mg of product as the bis-TFA salt. MH+ 469.3 (free base)

Workup

concentrationThe crude mixture was concentrated in vacuo
custompurified by preparative HPLC
additionThe purified intermediate product was then treated with 0.8 mL of 2N sodium hydroxide
stirringto stir for 36 hours
concentrationconcentrated in vacuo
customThe crude product was then purified by preparative HPLC (0-70% Acetonitrile/0.1% aq TFA)

Sources & evidence

ORD record: ord-7a8add4ae6c54dc69af0ffda1c4379ff
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919371B2

Reaction notes

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