Triethylamine → HCID 66786289, compound

HRID 1511462Notes

Reaction equation

HRID 1511462 reaction equation
Cl.[NH2:2][C@@H:3]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:4]([N:6]1[CH2:10][C@H:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][N:13]=2)[CH2:8][C@H:7]1[C:19]([NH:21][C@H:22]([CH:28]([OH:35])[C:29]([NH:31][CH:32]1[CH2:34][CH2:33]1)=[O:30])[CH2:23][CH:24]1[CH2:27][CH2:26][CH2:25]1)=[O:20])=[O:5].C(N(CC)CC)C.[C:47]([N:51]=[C:52]=[O:53])([CH3:50])([CH3:49])[CH3:48]>ClCCl>[C:47]([NH:51][C:52](=[O:53])[NH:2][C@@H:3]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:4]([N:6]1[CH2:10][C@H:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][N:13]=2)[CH2:8][C@H:7]1[C:19]([NH:21][C@H:22]([CH:28]([OH:35])[C:29]([NH:31][CH:32]1[CH2:33][CH2:34]1)=[O:30])[CH2:23][CH:24]1[CH2:27][CH2:26][CH2:25]1)=[O:20])=[O:5])([CH3:50])([CH3:49])[CH3:48]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 68907364HCID 68907364, compound

Product 1

HCID 66786289HCID 66786289, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (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 (45 mg, 0.077 mmol) in dichloromethane (3.0 mL) was added triethylamine (0.02 mL, 0.154 mmol). After 5 minutes at room temperature, tert-butylisocyanate (0.01 mL, 0.077 mmol) was added and the reaction mixture was stirred at room temperature. After 16 hours, the reaction mixture was diluted with dichloromethane and washed with 1N HCl, saturated sodium bicarbonate, and brine. The dichloromethane layer was then evaporated to dryness under reduced pressure to give (2S,4R)-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-4-(5-chloropyridin-2-yloxy)-N-((2S)-1-cyclobutyl-4-(cyclopropylamino)-3-hydroxy-4-oxobutan-2-yl)pyrrolidine-2-carboxamide.

Workup

  1. waitAfter 16 hours
  2. washwashed with 1N HCl, saturated sodium bicarbonate, and brine
  3. customThe dichloromethane layer was then evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-06a7c59089594319afb4e74656f26635
Source dataset
uspto-grants-2012_07
Patent number
US08211897B2

Reaction notes

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