Hydrochloric Acid → HCID 69058230, compound

HRID 859686Notes

Reaction equation

HRID 859686 reaction equation
[CH:1]1([C:6]2([CH2:26][CH2:27][C:28]3[CH:42]=[CH:41][C:31]([CH2:32][NH:33]C(=O)OC(C)(C)C)=[C:30]([CH2:43][CH3:44])[CH:29]=3)[CH2:11][C:10]([OH:12])=[C:9]([CH2:13][C:14]3[N:24]=[C:17]4[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)[C:8](=[O:25])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:45]>ClCCl.O1CCOCC1>[ClH:45].[NH2:33][CH2:32][C:31]1[CH:41]=[CH:42][C:28]([CH2:27][CH2:26][C:6]2([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[O:7][C:8](=[O:25])[C:9]([CH2:13][C:14]3[N:24]=[C:17]4[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)=[C:10]([OH:12])[CH2:11]2)=[CH:29][C:30]=1[CH2:43][CH3:44]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58764236HCID 58764236, compound

Product 1

HCID 69058230HCID 69058230, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-(2-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-ethylbenzylcarbamate (35 mg, 0.06 mmol, example A(126)) was dissolved in dichloromethane (1 mL) and 4N HCl in dioxane (0.5 mL) and stirred at room temperature 2 h. The solution was concentrated to give an off-white solid (30 mg, 96%). 1H NMR (300 MHz, CDCl3): δ ppm 1.14 (t, J=7.54 Hz, 3 H) 1.37–1.49 (m, 1 H) 1.52–1.66 (m, 6 H), 1.67–1.77 (m, 2 H) 2.05–2.16 (m, 2 H) 2.58 (s, 4 H) 2.60–2.70 (m, 6 H) 2.74–2.80 (m, 1 H), 3.80 (d, J=14.51 Hz, 2 H) 4.02 (q, J=5.78 Hz, 2 H) 7.07 (s, 1 H) 7.13 (s, 1 H) 7.16–7.21 (m, 1 H) 7.32 (d, J=7.72 Hz, 1 H) 8.15 (s, 3 H). MS (ESI): 504 (M+H)+.

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-8518da1d7cd24d73ba7b4b955f2c4119
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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