Hydrochloric Acid → HCID 86626190, compound

HRID 2355349Notes

Reaction equation

HRID 2355349 reaction equation
[CH:1]1([CH2:4][CH2:5][O:6][CH:7]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]3[C:17](=[O:18])[C:16](=[O:19])[C:15]=3[NH:20][C@@H:21]([CH2:33][CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:22][NH:23]C(=O)CCC[Si](C)(C)C)[CH2:9]2)[CH2:3][CH2:2]1.[ClH:46]>O1CCOCC1.CO>[ClH:46].[NH2:23][CH2:22][C@@H:21]([NH:20][C:15]1[C:16](=[O:19])[C:17](=[O:18])[C:14]=1[N:10]1[CH2:11][CH2:12][CH2:13][CH:8]([CH:7]([O:6][CH2:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:9]1)[CH2:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86626191HCID 86626191, compound

Product 1

HCID 86626190HCID 86626190, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

The N—((S)-2-(2-(3-((2-cyclopropylethoxy)(phenyl)methyl)piperidin-1-yl)-3,4-dioxocyclobut-1-enylamino)-3-cyclohexylpropyl)-4-(trimethylsilyl)butanamide (12.3 mg, 0.02 mmol) was dissolved in dioxane (1 mL) and treated with 4M HCl in dioxane (0.5 mL, 2.0 mmol). The solution was allowed to stir for 1.5 h before evaporation of solvent. The residual oil was redissolved in methanol and evaporated under reduced pressure to afford 3-((S)-1-amino-3-cyclohexylpropan-2-ylamino)-4-(3-((2-cyclopropylethoxy)(phenyl)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione hydrochloride as an oil (10 mg, >99%). MS ESI+ve m/z 494 (M+1).

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b1fe08d03cf44625a0521a2b007c82e4
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

Loading…