Acetic Anhydride → HCID 131725115, compound

HRID 586819Notes

Reaction equation

HRID 586819 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].F[C:16](F)(F)[C:17]([OH:19])=O.CC1C=C(CO[C:35]2[CH:40]=[CH:39][C:38]([C:41]3([N:50]4[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]4)[C:46](=[O:47])[NH:45][C:44](=[O:48])[NH:43][C:42]3=[O:49])=[CH:37][CH:36]=2)C2C(=CC=CC=2)N=1.[CH:56]([N:59](CC)[CH:60]([CH3:62])[CH3:61])([CH3:58])[CH3:57].C(O[C:69](=O)[CH3:70])(=O)C.[C:72]([O-])(O)=O.[Na+]>ClCCl.C(OCC)(=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[C:17]([N:53]1[CH2:54][CH2:55][N:50]([C:41]2([C:38]3[CH:39]=[CH:40][C:35]([O:5][CH2:3][C:2]4[C:61]5[C:60](=[CH:62][CH:72]=[CH:69][CH:70]=5)[N:59]=[C:56]([CH3:57])[CH:58]=4)=[CH:36][CH:37]=3)[C:42](=[O:49])[NH:43][C:44](=[O:48])[NH:45][C:46]2=[O:47])[CH2:51][CH2:52]1)(=[O:19])[CH3:16]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 131725107HCID 131725107, compound

Product 1

HCID 131725115HCID 131725115, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 14 (120 mg, 0.150 mmol) was treated with N,N-diisopropylethylamine (0.13 mL, 5.0 eq) and acetic anhydride (30.6 mg, 2.0 eq) in dichloromethane (5 mL) at rt. After 1 h at rt, saturated NaHCO3 (5 mL) and ethyl acetate (100 mL) were added. The mixture was washed with water (2×5 mL), brine (5 mL), dried (MgSO4) and concentrated in vacuo. Purification by reverse phase HPLC (gradient elution, water/acetonitrile 80-20 to 20-80, 0.1% TFA) provided the title barbituric acid (75.4 mg, 69%). MS found: (M+H)+=502.

Workup

  1. washThe mixture was washed with water (2×5 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification
  5. washby reverse phase HPLC (gradient elution, water/acetonitrile 80-20 to 20-80, 0.1% TFA)

Sources & evidence

ORD record
ord-935309166ac7497f9180d01e6482e4a3
Source dataset
uspto-grants-2005_08
Patent number
US06936620B2

Reaction notes

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