Hydrochloric Acid → HCID 59118247, compound

HRID 432101Notes

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:30]3[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=3)[C:33]([OH:35])=[O:34])[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.C(O)(C(F)(F)F)=O>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:30]3[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=3)[C:33]([OH:35])=[O:34])[CH:25]=2)[O:20]1

Participants

Conditions

Temperature: 45 °C

Procedure

To 670 mg (1.25 mmol) of crude 3-{[(2R)-2-({(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]sulfanyl}benzoic acid (Example 173) diluted in 5 mL 1,4-dioxane, was added 0.5 mL of 6N hydrochloric acid slowly. The resulting mixture was stirred at 45° C. for 2 hours. After this time the mixture was concentrated in vacuo, dissolved in 2 mL of 1:1 methanol to water, and purified by HPLC (0-70% acetonitrile/0.1% TFA) to afford 28.5 mg (5% yield) of the desired product as the bis TFA salt. MH+ 437.3. 1H NMR (CDCl3, δ): 8.91 (br. S, 1H), 8.63 (d, 1H), 8.56 (dd, 1H), 7.89 (m, 1H), 7.72 (dt, 1H), 7.62 (m, 1H), 7.49 (m, 1H), 7.39 (m, 1H), 7.31 (m, 1H), 7.27 (m, 1H), 7.24 (dd, 1H), 6.90 (d, 1H), 6.35 (br. S, 1H), 5.07 (m, 1H), 4.48 (m, 1H), 3.32 (m, 4H), 3.16 (m, 1H), 2.78 (m, 2H), 2.04 (m, 1H), 1.71 (m, 1H).

Workup

concentrationAfter this time the mixture was concentrated in vacuo
dissolutiondissolved in 2 mL of 1:1 methanol to water
custompurified by HPLC (0-70% acetonitrile/0.1% TFA)

Sources & evidence

ORD record: ord-b6627c52d91e433e8a0916d1eef29035
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660752B2

Reaction notes

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