HCID 86752823, compound → HCID 67649043, compound

HRID 964722Notes

Reaction equation

HRID 964722 reaction equation
[P:1](=[O:93])([S:84][CH2:85][O:86][C:87](=[O:92])[C:88]([CH3:91])([CH3:90])[CH3:89])([O:43][CH:44]([OH:83])[C@H:45]1[O:49][C@@H:48]([N:50]2[CH:58]=[C:56]([CH3:57])[C:54](=[O:55])[NH:53][C:51]2=[O:52])[CH2:47][C@@H:46]1[O:59]C(C1C=CC=CC=1)(C1C=CC(OC)=CC=1)C1C=CC(OC)=CC=1)[O:2][C@@:3]1([OH:42])[C@@H:7]([CH2:8][O:9]C(C2C=CC=CC=2)(C2C=CC(OC)=CC=2)C2C=CC(OC)=CC=2)[O:6][C@@H:5]([N:33]2[CH:41]=[C:39]([CH3:40])[C:37](=[O:38])[NH:36][C:34]2=[O:35])[CH2:4]1>C(O)(=O)C.O.CO>[P:1](=[O:93])([S:84][CH2:85][O:86][C:87](=[O:92])[C:88]([CH3:91])([CH3:90])[CH3:89])([O:43][CH:44]([OH:83])[C@H:45]1[O:49][C@@H:48]([N:50]2[CH:58]=[C:56]([CH3:57])[C:54](=[O:55])[NH:53][C:51]2=[O:52])[CH2:47][C@@H:46]1[OH:59])[O:2][C@@:3]1([OH:42])[C@@H:7]([CH2:8][OH:9])[O:6][C@@H:5]([N:33]2[CH:41]=[C:39]([CH3:40])[C:37](=[O:38])[NH:36][C:34]2=[O:35])[CH2:4]1

Participants

3

Reactant 1

HCID 86752823HCID 86752823, compound

Product 1

HCID 67649043HCID 67649043, compound

Reagents, catalysts & solvents 1

HCID 86607755Acetic acid methanol waterSolvent

Procedure

The totally protected dimeric phosphorothioate triester (3a) is dissolved in a mixture of acetic acid/water/methanol (8:1:1, v:v:v) (10 ml). The reaction is left with stirring at ambient temperature for 5 hours. The reaction medium is then evaporated and the residue is coevaporated several times with water and toluene. The residue is then chromatographed on a silica gel column using a gradient of methanol (0 to 10%) in dichloro-methane as eluent. The fractions containing the product (4a) are collected, concentrated under reduced pressure, and then the residue is coevaporated several times with dioxane and lyophilized in dioxane. (4a) is obtained in the form of a white powder (98 mg, 85%).

Workup

  1. waitThe reaction is left
  2. customThe reaction medium is then evaporated
  3. customThe residue is then chromatographed on a silica gel column
  4. additionThe fractions containing the product (4a)
  5. customare collected
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39127010b2a043af846625fa5dfb7dba
Source dataset
uspto-grants-1998_06
Patent number
US05770713

Reaction notes

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