Ammonia → HCID 69539402, compound

HRID 2416145Notes

Reaction equation

HRID 2416145 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:7])=[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.[NH3:70]>CC(O)C.C(N(CC)CC)C.C(#N)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:70]3[CH:38]=[CH:36][C:35]([NH2:53])=[N:44][C:45]3=[O:46])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 6029UridineHCID 73974-Toluenesulfonyl chlorideHCID 12291N-MethylpiperidineHCID 69539405HCID 69539405, compound

Product 1

HCID 69539402HCID 69539402, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To 1.0 g of 3′,5′-O-bis (4-chlorobenzoyl)-2′-deoxyuridine was added 5 mL of acetonitrile, 0.40 g of triethylamine, 0.24 g (1.2 times moles based on the uridine derivative) of 1-methylpiperidine and 0.76 g of p-toluenesulfonyl chloride, and the reaction mixture was stirred in an ice bath for 2 hours. To this, 7.5 mL of a solution of ammonia in 2-propanol was added, and the mixture was stirred in an ice bath for 4 hours, and at room temperature for 1 hour. The crystals were filtered and washed with acetonitrile to give 0.54 g of 3′,5′-O-bis(4-chlorobenzoyl)-2′-deoxycytidine. Yield 54%.

Workup

  1. stirringthe mixture was stirred in an ice bath for 4 hours
  2. waitat room temperature for 1 hour
  3. filtrationThe crystals were filtered
  4. washwashed with acetonitrile

Sources & evidence

ORD record
ord-91b52cbdb84c47e4a2dd6c5bd92e10c2
Source dataset
uspto-grants-2004_11
Patent number
US06822090B2

Reaction notes

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