Hydrochloric Acid → HCID 68907364, compound

HRID 1511461Notes

Reaction equation

HRID 1511461 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C@H:9]2[CH2:13][N:12]([C:14](=[O:28])[C@@H:15]([NH:20]C(=O)OC(C)(C)C)[C:16]([CH3:19])([CH3:18])[CH3:17])[C@H:11]([C:29](=[O:45])[NH:30][C@H:31]([CH:37]([OH:44])[C:38]([NH:40][CH:41]3[CH2:43][CH2:42]3)=[O:39])[CH2:32][CH:33]3[CH2:36][CH2:35][CH2:34]3)[CH2:10]2)=[N:6][CH:7]=1.Cl>ClCCl.O1CCOCC1>[ClH:1].[NH2:20][C@@H:15]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]([N:12]1[CH2:13][C@H:9]([O:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)[CH2:10][C@H:11]1[C:29]([NH:30][C@H:31]([CH:37]([OH:44])[C:38]([NH:40][CH:41]1[CH2:42][CH2:43]1)=[O:39])[CH2:32][CH:33]1[CH2:36][CH2:35][CH2:34]1)=[O:45])=[O:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71210458HCID 71210458, compound

Product 1

HCID 68907364HCID 68907364, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl (2S)-1-((2S,4R)-4-(5-chloro-pyridin-2-yloxy)-2-((2S)-1-cyclobutyl-4-(cyclopropylamino)-3-hydroxy-4-oxobutan-2-ylcarbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (313 mg, 0.482 mmol) in dichloromethane (2 mL) was added 4.0 M HCl in dioxane (3.0 mL). After 1 hour, the reaction mixture was concentrated under reduced pressure and dried to give (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-(5-chloro-pyridin-2-yloxy)-N-((2S)-1-cyclobutyl-4-(cyclopropylamino)-3-hydroxy-4-oxobutan-2-yl)pyrrolidine-2-carboxamide HCl salt as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customdried

Sources & evidence

ORD record
ord-25cb75eaff034e2da10add5a3f619e96
Source dataset
uspto-grants-2012_07
Patent number
US08211897B2

Reaction notes

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