Hydrochloric Acid → HCID 59118210, compound

HRID 896869Notes

Reaction equation

HRID 896869 reaction equation
CC([Si](C)(C)[O:6][C@H:7]([C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)[CH2:8][N:9]([CH2:17][C@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([C:34]([OH:36])=[O:35])[CH:29]=3)[CH:24]=2)[O:19]1)C(OC(C)(C)C)=O)(C)C.Cl>O1CCOCC1>[OH:6][C@H:7]([C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)[CH2:8][NH:9][CH2:17][C@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([C:34]([OH:36])=[O:35])[CH:29]=3)[CH:24]=2)[O:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59118177HCID 59118177, compound

Product 1

HCID 59118210HCID 59118210, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-{(2R)-2-[([(2R)-2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}-2-(3-pyridinyl)ethyl]{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-3,4-dihydro-2H-chromen-6-yl}-2-pyridinecarboxylic acid (Example 70, 29 mg, 0.05 mmol) was stirred in an excess of 4M HCl in dioxane at room temperature for 18 hours. The volatile components were removed by rotary evaporation, and the residue was washed with dichloromethane. After drying under vacuum, the title compound was collected as the tri-hydrochloride salt (23 mg, 93%): 1H NMR (300 MHz, CD3OD) δ 9.07 (broad s, 1 H), 8.90 (d, 1 H), 8.83-8.78 (m, 3 H), 8.49 (d, 1 H), 8.18 (t, 1 H), 7.94-7.89 (m, 2 H), 7.20 (d, 1 H), 5.52-5.46 (m, 1 H), 4.67-4.61 (m, 1 H), 3.76-3.57 (m, 2 H), 3.51-3.39 (m, 2 H), 3.10-3.05 (m, 2 H), 2.29-2.20 (m, 1 H), 1.95-1.83 (m, 1 H); MS m/z 406.2 (MH+ of the free base).

Workup

  1. customThe volatile components were removed by rotary evaporation
  2. washthe residue was washed with dichloromethane
  3. customAfter drying under vacuum
  4. customthe title compound was collected as the tri-hydrochloride salt (23 mg, 93%)

Sources & evidence

ORD record
ord-c785cc19d7e94817b15600bd5070cb75
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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