Ammonium Carbonate → HCID 67523147, compound

HRID 1454946Notes

Reaction equation

HRID 1454946 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:43])[CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[C:18]([N:28]3[CH2:33][CH2:32][CH2:31][CH:30]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:29]3)=[N:17][C:16]=2[N:15]([CH3:42])[C:13]1=[O:14])([OH:3])=O.C(=O)([O-])[O-].[NH4+].[NH4+].[N:50]1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[B-](F)(F)F.OC1C2N=NNC=2C=CC=1>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[OH:43][C:10]1([CH2:11][N:12]2[C:21](=[O:22])[C:20]3[N:19]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[C:18]([N:28]4[CH2:33][CH2:32][CH2:31][CH:30]([NH:34][C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[CH2:29]4)=[N:17][C:16]=3[N:15]([CH3:42])[C:13]2=[O:14])[C:5]2[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[O:3])[NH:50]1

Participants

8

Reactant 4

HCID 517111Ammonium CarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66754105HCID 66754105, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 67523147HCID 67523147, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 250 mg of 1-[2-(2-carboxy-phenyl)-2-oxo-ethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-[3-(tert.-butyloxycarbonyl-amino)-piperidin-1-yl]-xanthine, 404 mg of ammonium carbonate, 135 mg of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-tetrafluoroborate, 57 mg of hydroxybenzotriazole and 59 μl of triethylamine in 3 ml of tetrahydrofuran is stirred for eight hours at ambient temperature. For working up the reaction mixture is diluted with 30 ml of ethyl acetate and washed with 10% citric acid solution, 10% potassium carbonate solution and saturated sodium chloride solution. The organic phase is evaporated down and chromatographed through a silica gel column with methylene chloride/methanol (98:2 to 80:20).

Workup

  1. washwashed with 10% citric acid solution, 10% potassium carbonate solution and saturated sodium chloride solution
  2. customThe organic phase is evaporated down
  3. customchromatographed through a silica gel column with methylene chloride/methanol (98:2 to 80:20)

Sources & evidence

ORD record
ord-32e261ca51d1466c904c6f4ec47f6d75
Source dataset
uspto-grants-2009_01
Patent number
US07482337B2

Reaction notes

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