Chloroform → HCID 69539402, compound

HRID 2416147Notes

Reaction equation

HRID 2416147 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([C@@:8]2([OH:32])[C@@H:12]([CH2:13][O:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20]C(Cl)=[CH:18][CH:17]=3)[O:11][C@@H:10]([N:24]3[CH:31]=[CH:30][C:28](=O)[NH:27][C:25]3=[O:26])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH:35]([Cl:38])(Cl)Cl.[N:39]12CCN(CC1)CC2.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@@:8]2([OH:32])[C@@H:12]([CH2:13][O:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:35]([Cl:38])=[CH:18][CH:17]=3)[O:11][C@@H:10]([N:24]3[CH:31]=[CH:30][C:28]([NH2:39])=[N:27][C:25]3=[O:26])[CH2:9]2)=[O:7])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 69539405HCID 69539405, compound

Product 1

HCID 69539402HCID 69539402, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 3.0 g of 3′,5′-O-bis(4-chlorobenzoyl)-2′-deoxyuridine was added 30 mL of chloroform, 0.72 g of triethylamine, 0.80 g (1.2 times moles of uridine derivative) of 1,4-diazabicyclo[2.2.2]octane and 1.36g of p-toluenesulfonyl chloride, and the resulting mixture was stirred at room temperature for 30 minutes. Ammonia gas was bubbled into the reaction mixture at room temperature for 1 hour, and the mixture was stirred in an ice bath for 1 hour. After sludging by the addition of 100 mL of water and 100 mL of methanol, the crystals were filtered and washed with the mixed solution of water and methanol (1:1) to give 2.42 g of 3′,5′-O-bis(4-chlorobenzoyl)-2′-deoxycytidine. Yield 80.9%.

Workup

  1. customAmmonia gas was bubbled into the reaction mixture at room temperature for 1 hour
  2. stirringthe mixture was stirred in an ice bath for 1 hour
  3. additionAfter sludging by the addition of 100 mL of water and 100 mL of methanol
  4. filtrationthe crystals were filtered
  5. washwashed with the mixed solution of water and methanol (1:1)

Sources & evidence

ORD record
ord-8bb5f2d8a5be4b48be30e40e256b24e2
Source dataset
uspto-grants-2004_11
Patent number
US06822090B2

Reaction notes

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