Water → HCID 11555432, compound

HRID 891009Notes

Reaction equation

HRID 891009 reaction equation
[C@@H:1]1([N:12]2[C:16]3[C:17]4[NH:18][C:19]5[C:24]([C:25]=4[C:26]4[C:30](=[O:31])[N:29]([CH3:32])[C:28](=[O:33])[C:27]=4[C:15]=3[C:14]3[CH:34]=[CH:35][CH:36]=[N:37][C:13]2=3)=[CH:23][CH:22]=[CH:21][CH:20]=5)[O:9][C@H:8]([CH2:10]O)[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:58].O>N1C=CC=CC=1>[Cl:58][CH2:10][C@H:8]1[O:9][C@@H:1]([N:12]2[C:16]3[C:17]4[NH:18][C:19]5[C:24]([C:25]=4[C:26]4[C:30](=[O:31])[N:29]([CH3:32])[C:28](=[O:33])[C:27]=4[C:15]=3[C:14]3[CH:34]=[CH:35][CH:36]=[N:37][C:13]2=3)=[CH:23][CH:22]=[CH:21][CH:20]=5)[C@H:2]([OH:3])[C@@H:4]([OH:5])[C@@H:6]1[OH:7]

Participants

6

Reactant 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 11813112HCID 11813112, compound

Product 1

HCID 11555432HCID 11555432, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the compound of Example 17 (0.353 mmol) dissolved in 2.5 ml of pyridine there is added a solution of triphenylphosphine (1.415 mmol) and then carbon tetrachloride (0.707 mmol). The mixture is stirred at ambient temperature for 2.30 hours and is then poured into water. The mixture is extracted with ethyl acetate and the organic phase is washed successively with a 1N aqueous solution of hydrochloric acid, water and a saturated solution of NaHCO3. After evaporating off the solvent and then purifying by chromatography over silica gel (ethyl acetate), the expected product is isolated.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washthe organic phase is washed successively with a 1N aqueous solution of hydrochloric acid, water
  3. customAfter evaporating off the solvent
  4. custompurifying by chromatography over silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-38b8095ddf9d4da2a58cc0df7c3f1e05
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Reaction notes

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