Hydrochloric Acid → HCID 131731995, compound

HRID 331087Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:41])[CH2:13][CH2:12][N:11]([C:14](=[O:38])[C@H:15]([NH:19][C:20]([C@@H:22]3[CH2:26][CH2:25][C:24]([NH:30]C(=O)OC(C)(C)C)([CH2:27][CH2:28][OH:29])[CH2:23]3)=[O:21])[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:40])[CH3:39])=[CH:4][CH:3]=1.Cl>>[Cl-:1].[NH2:30][C:24]1([CH2:27][CH2:28][OH:29])[CH2:25][CH2:26][C@@H:22]([C:20]([NH:19][C@H:15]([CH:16]([CH3:18])[CH3:17])[C:14]([N:11]2[CH2:12][CH2:13][C@@:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([OH:41])[C:9]([CH3:40])([CH3:39])[CH2:10]2)=[O:38])=[O:21])[CH2:23]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 68179150HCID 68179150, compound

Product 1

HCID 131731995HCID 131731995, compoundYield 191.8%

Procedure

To t-butyl(3R)-3-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamoyl)-1-(2-hydroxyethyl)cyclopentylcarbamate (58 mg, 0.098 mmol) was added hydrogen chloride (4M in dioxane, 0.5 mL). The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated to yield (1R)-3-amino-N—((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-3-(2-hydroxyethyl)cyclopentanecarboxamide, hydrogen chloride salt (50 mg, 0.094 mmol, 97% yield) as an oil. It was used as such for the next step without further purification. MS (ESI+) m/z 494 M+

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-4367b2b7b12b43d391dadf0ffaee3ee5
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877749B2

Reaction notes

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