Barbituric Acid → HCID 86590601, compound

HRID 1824429Notes

Reaction equation

HRID 1824429 reaction equation
C(O[C:5](=[O:16])[NH:6][CH:7]1[CH2:11][C:10](=[O:12])[O:9][CH:8]1[O:13]CC)C=C.N1C(=O)CC(=O)NC1=O.[C:26]([NH:34][CH:35]1[C:42](=[O:43])[N:41]2[CH:44](C(O)=O)[CH2:45][CH2:46][CH:40]2[CH2:39][CH:38](C)[CH2:37][CH2:36]1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(O)(C(F)(F)F)=O>ClCCl.O>[OH:13][CH:8]1[CH:7]([NH:6][C:5]([C@H:44]2[N:41]3[C:42](=[O:43])[C@@H:35]([NH:34][C:26](=[O:33])[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:36][CH2:37][CH2:38][CH2:39][C@H:40]3[CH2:46][CH2:45]2)=[O:16])[CH2:11][C:10](=[O:12])[O:9]1

Participants

9

Reactant 6

HCID 6211Barbituric AcidHCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22149038(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl esterHCID 22149123HCID 22149123, compound

Product 1

HCID 86590601HCID 86590601, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2-Ethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester (183 mg, 0.8 mmol) in dichloromethane (6 mL) is added barbituric acid (300 mg, 1.9 mmol) and tetrakis triphenylphosphine palladium (92 mg, 0.08 mmol). The solution is stirred for 10 minutes and 6-benzoylamino-9-methyl-5-oxo-decahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid, 20, (105 mg, 0.32 mmol) is added followed by HOBt (99 mg, 0.74 mmol) and EDCI (141 mg, 0.74 mmol). The solution is stirred for 6 hours. Water is added and the organics are washed with NaHSO4, Brine, NaHCO3, and water. The organics are dried with MgSO4 and concentrated under reduced pressure. The residue is purified over silica to afford an oil which is dissolved in dichloromethane and treated with TFA (5 mL) and water (1 mL). The solution is stirred for 2 hours and the solvent is removed. The residue is purified over silica to afford the desired product as a white powder. 1H NMR (CDCl3): δ 7.83 (m, 2H), 7.56–7.39 (m, 3H), 7.26 (m, 2H), 5.51 (d, J=5.2, 1H), 5.16 (m,1H), 4.72 (m, 1H), 4.56 (t, J=8.1 Hz, 1H), 4.35 (m, 1H), 3.95 (m, 1H), 3.71 (m, 2H), 2.90 (m, 1H), 2.52–2.38 (m, 2H), 2.26–2.05 (m, 4H), 1.87–1.61 (m, 5H), 1.32 (t, J=6.9 Hz, 3H). 13C NMR (CDCl3): δ 173.7, 172.2, 171.7, 166.6, 131.9, 128.8, 127.3, 101.3, 65.9, 60.8, 59.5, 50.6, 48.6, 36.9, 36.3, 33.1, 32.4, 25.7, 25.6, 23.6, 15.2. ESI MS: 458.16 (M+H), 480.11 (M+Na).

Workup

  1. stirringThe solution is stirred for 6 hours
  2. washthe organics are washed with NaHSO4, Brine, NaHCO3, and water
  3. dry with materialThe organics are dried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified over silica
  6. customto afford an oil which
  7. stirringThe solution is stirred for 2 hours
  8. customthe solvent is removed
  9. customThe residue is purified over silica

Sources & evidence

ORD record
ord-e74f93d9fece492cb7ed8bb1f44cb9e7
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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