Carbon tetrabromide → HCID 18633464, compound

HRID 232356Notes

Reaction equation

HRID 232356 reaction equation
[C:1]([NH:9][C:10]1[C:23]([CH2:24][CH3:25])=[CH:22][N:13]([C@@H:14]2[O:21][C@H:18]([CH2:19]O)[C@@H:16]([OH:17])[CH2:15]2)[C:12](=[O:26])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:46]=[N+:47]=[N-:48].[Na+].C(Br)(Br)(Br)Br>CN(C)C=O.CO>[N:46]([CH2:19][C@H:18]1[O:21][C@@H:14]([N:13]2[CH:22]=[C:23]([CH2:24][CH3:25])[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:11][C:12]2=[O:26])[CH2:15][C@@H:16]1[OH:17])=[N+:47]=[N-:48]

Participants

7

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 18633452HCID 18633452, compound

Product 1

HCID 18633464HCID 18633464, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.436 g of N-benzoyl-2'-deoxy-5-ethylcytidine, 1.072 g of triphenylphosphine, 1.304 g of sodium azide and 1.360 g of carbon tetrabromide in 16 ml of dimethylformamide was stirred at room temperature for 20 hours. 8 ml of methanol were added, the mixture was stirred for 30 minutes and then evaporated. The residue was suspended in 80 ml of water and extracted three times with 100 ml of ethyl acetate each time. The combined ethyl acetate extracts were washed with water and evaporated. The residue was subjected to flash chromatography on a column of silica gel using ethyl acetate for the elution, there being obtained 1 g of 5'-azido-4-N-benzoyl-2',5'-dideoxy-5-ethylcytidine in the form of a white crystalline solid of melting point 125°-126° C.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customevaporated
  3. extractionextracted three times with 100 ml of ethyl acetate each time
  4. washThe combined ethyl acetate extracts were washed with water
  5. customevaporated
  6. washfor the elution, there

Sources & evidence

ORD record
ord-5798cc57b3d144baba35d2711488fd63
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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