Sodium Carbonate → HCID 59568627, compound

HRID 216970Notes

Reaction equation

HRID 216970 reaction equation
[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([S:37]([C:40]2[CH:45]=[CH:44][C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][CH:41]=2)(=[O:39])=[O:38])[CH2:33][CH2:32]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:43]2[CH:44]=[CH:45][C:40]([S:37]([N:34]3[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]3)(=[O:38])=[O:39])=[CH:41][CH:42]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 231545021-Methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonyl]piperazineHCID 59568595(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 59568627HCID 59568627, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 250 mg) and 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylsulfonyl)piperazine (177 mg) in acetonitrile (8 mL) was treated with aqueous sodium carbonate solution (2M, 0.483 mL) and then nitrogen was bubbled through the mixture. 1,1 bis(Di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added and the mixture was heated at 85° C. under nitrogen for 18 h. The mixture was purified by chromatography on silica eluting with ethyl acetate/isohexane (70:10 to 100:0), then methanol/ethyl acetate (5:95) and then methanol/ethyl acetate/triethylamine (5:95:1) to afford the sub-titled compound (267 mg).

Workup

  1. customnitrogen was bubbled through the mixture
  2. addition1,1 bis(Di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added
  3. customThe mixture was purified by chromatography on silica eluting with ethyl acetate/isohexane (70:10 to 100:0)

Sources & evidence

ORD record
ord-293318dcbc3c49f5ac8d2288aec898a4
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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