Uridine → HCID 69539402, compound

HRID 2416143Notes

Reaction equation

HRID 2416143 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:19]([Cl:22])=[CH:18][CH:17]=3)[O:11][C@@H:10](N3C=CC(=O)NC3=O)[CH2:9]2)=O)=[CH:4][CH:3]=1.[C@@H:35]1([N:44]2C=CC(=O)N[C:45]2=[O:46])O[C@H](CO)[C@@H:38](O)[C@H:36]1O.C[N:53]1CCCCC1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH2:70].[NH3:71]>C(#N)C.C(N(CC)CC)C>[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:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[O:11][C@@H:10]([N:71]3[CH:38]=[CH:36][C:35]([NH2:53])=[N:44][C:45]3=[O:46])[CH2:9]2)=[O:70])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6029UridineHCID 73974-Toluenesulfonyl chlorideHCID 12291N-MethylpiperidineHCID 12896473Azane;hydrateHCID 69539405HCID 69539405, compound

Product 1

HCID 69539402HCID 69539402, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 10.0 g of 3′,5′-O-bis(4-chlorobenzoyl)-2′-deoxyuridine was added 50 mL of acetonitrile, 4.0 g of triethylamine, and 2.4 g (1.2 times moles based on the uridine derivative) of 1-methylpiperidine, and the resulting mixture was stirred in an ice bath. To this, the solution of 7.5 g of p-toluenesulfonyl chloride in 25 ml of acetonitrile was added dropwise over 1 hour at −1.5° C. or below −1.5° C. After the completion of addition, the mixture was stirred for 1 hour. Then, 50 mL of 28% ammonia water was added dropwise over 20 minutes at 4.5° C. or below 4.5° C. After the completion of addition, the mixture was stirred for 2.5 hours. The precipitated crystals were filtered and washed with acetonitrile to give 7.93 g of 3′,5′-O-bis(4-chlorobenzoyl) -2′-deoxycytidine. Yield 79.5%.

Workup

  1. additionAfter the completion of addition
  2. stirringthe mixture was stirred for 1 hour
  3. additionAfter the completion of addition
  4. stirringthe mixture was stirred for 2.5 hours
  5. filtrationThe precipitated crystals were filtered
  6. washwashed with acetonitrile

Sources & evidence

ORD record
ord-3684fadc1cf6401795f3217b4ab0bf8c
Source dataset
uspto-grants-2004_11
Patent number
US06822090B2

Reaction notes

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