HCID 57370091, compound → HCID 29977151, compound

HRID 1834894Notes

Reaction equation

HRID 1834894 reaction equation
[CH3:1][C:2]1([CH3:21])[O:9][CH:8]2[C@H:4]([C@@H:5]([CH2:19]I)[O:6][C@H:7]2[N:10]2[C:15](=[O:16])[N:14]=[C:13]([NH2:17])[C:12]([F:18])=[CH:11]2)[O:3]1.[H][H]>CO.C(N(CC)CC)C.[Pd]>[CH3:19][C@H:5]1[O:6][C@@H:7]([N:10]2[C:15](=[O:16])[N:14]=[C:13]([NH2:17])[C:12]([F:18])=[CH:11]2)[C@@H:8]2[O:9][C:2]([CH3:1])([CH3:21])[O:3][C@@H:4]12

Participants

6

Reactant 2

HCID 57370091HCID 57370091, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 29977151HCID 29977151, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5'-deoxy-5'-iodo-2',3'-O-isopropylidene-5-fluorocytidine (48g, 116.5 mmol) in methanol (500 ml) and triethylamine (20ml) was treated with hydrogen at atmospheric pressure in the presence of palladium on carbon (5%, 25g) for 30 min. at room temperature. During this time the suspension was agitated using a "VIBROMIX" vibrator. The catalyst removed by filtration through celite, and the filtrate was evaporated to dryness and triturated with ethyl acetate (200 ml). After storage overnight the crystals were removed by filtration, and the filtrate was evaporated to approximately 100 ml and again stored overnight. A second batch of crystals was removed by filtration, and the filtrate was evaporated to dryness, pumped in vacuo, to give 5'-deoxy-2',3'-O-isopropylidene-5-fluorocytidine as a foam 31g (93%). This material was characterized by formation of a crystalline picrate salt, mp 168°-170°. uv (CH3OH) λ max 237-238 mμ(ε 20,700), λmax 282 mμ(ε 9,400), λ max 353-354mμ(ε 15,300). NMR ((CH3)2SO-d6) δ 8.58 (S, 2, picrate) δ 8.29 (d, 1, J = 7 Hz, CHCF) δ5.72 (d,J= 4 Hz, C'1) δ1.47, 1.28 (S, 3, (CH3)2C) δ 1.31 (d, 3, J = 6 Hz, CH3CH).

Workup

  1. customThe catalyst removed by filtration through celite
  2. customthe filtrate was evaporated to dryness
  3. customtriturated with ethyl acetate (200 ml)
  4. customAfter storage overnight the crystals were removed by filtration
  5. customthe filtrate was evaporated to approximately 100 ml and again stored overnight
  6. customA second batch of crystals was removed by filtration
  7. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-8c7f3586828944be91841ddcdce6c20a
Source dataset
uspto-grants-1978_01
Patent number
US04071680

Reaction notes

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