Hydrochloric Acid → HCID 59118210, compound

HRID 432092Notes

Reaction equation

HRID 432092 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, 1H), 8.90 (d, 1H), 8.83-8.78 (m, 3H), 8.49 (d, 1H), 8.18 (t, 1H), 7.94-7.89 (m, 2H), 7.20 (d, 1H), 5.52-5.46 (m, 1H), 4.67-4.61 (m, 1H), 3.76-3.57 (m, 2H), 3.51-3.39 (m, 2H), 3.10-3.05 (m, 2H), 2.29-2.20 (m, 1H), 1.95-1.83 (m, 1H); 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-dc162bf408724b2f8e18b3a14d912fee
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

Loading…