Triethylamine → HCID 69745989, compound

HRID 1063772Notes

Reaction equation

HRID 1063772 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 (219 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 18 h, 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) δ 2.10 (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=65 Hz), 6.78 (m, 2H), 7.30 (m 2), 8.05 (s, 1H).

Workup

  1. stirringthe solution was stirred for 1 h
  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-9b12cc22ca7844a18c16a1af5c760766
Source dataset
uspto-grants-2005_11
Patent number
US06967079B2

Reaction notes

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