Triethylamine → HCID 69745989, compound

HRID 1167395Notes

Reaction equation

HRID 1167395 reaction equation
[C:1]([C@@:4]1([OH:23])[C@@H:8]([CH:9]([C:11](=[O:13])[CH3:12])[OH:10])[O:7][C@@H:6]([N:14]2[CH:21]=[C:20]([I:22])[C:18](=O)[NH:17][C:15]2=[O:16])[CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.C1(C)C=C(C)C=C(C)C=1S(Cl)(=O)=O.C1CCN2C(=NCCC2)CC1.[NH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[SH:62]>CN(C1C=CN=CC=1)C>[I:22][C:20]1[C:18]([NH:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=2[SH:62])=[N:17][C:15](=[O:16])[N:14]([CH:21]=1)[C@@H:6]1[O:7][C@H:8]([CH:9]([C:11](=[O:13])[CH3:12])[OH:10])[C@@:4]([C:1](=[O:3])[CH3:2])([OH:23])[CH2:5]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 87132-AminothiophenolHCID 130462-Mesitylenesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69723565HCID 69723565, compound

Product 1

HCID 69745989HCID 69745989, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 3′,5′-diacetyl-5-iodo-2′-deoxyuridine (2.19 g, 5.00 mmol) acetonitrile (ACN, 75 ml), triethylamine (TEA, 6.96 ml, 50.0 mmol) and DMAP (0.15 g, 1.25 mmol) was added mesitylsulfonyl chloride (2.19 g, 10.0 mmol). After stirring at ambient temperature for 18h, DBU (2.14 ml, 10.0 mmol) and 2-aminothiophenol was added (2.14 g, 20.0 mmol) and the solution was stirred for 1 h. The reaction mixture was concentrated and the crude product was partitioned between ethyl acetate (EA, 200 ml) and saturated aqueous sodium bicarbonate (SASB, 200 ml). The organic layer was dried (Na2SO4) and concentrated on the rotary evaporator. The crude product was purified by flash chromatography on silica gel [1-5% 2-propanol/dichloromethane (DCM)] to deliver the product 1H NMR (CDCl3) δ2.10 (s, 3H), 2.15 (m, 1H, 2.17 (s, 3H 2.77 (ddd, 1H, J=2.2, 5.2,15.1 Hz), 4.14 (bs, 1H), 4.35 (m, 3H), 5.20 (m, 1H), 6.13 (t, 1H, J=6.5 Hz), 6.78 (m, 2H), 7.30 (m, 2H), 8.05 (s, 1H).

Workup

  1. additionwas added (2.14 g, 20.0 mmol)
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude product was partitioned between ethyl acetate (EA, 200 ml) and saturated aqueous sodium bicarbonate (SASB, 200 ml)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated on the rotary evaporator
  6. customThe crude product was purified by flash chromatography on silica gel [1-5% 2-propanol/dichloromethane (DCM)]

Sources & evidence

ORD record
ord-f6751da5bd3b4e769b8a667ea917c33d
Source dataset
uspto-grants-2003_09
Patent number
US06617437B1

Reaction notes

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