HCID 57370091, 화합물 → HCID 29977151, 화합물

HRID 1834894노트

반응식

HRID 1834894 반응식
[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

참가 물질

6

반응물 2

HCID 57370091HCID 57370091, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 29977151HCID 29977151, 화합물

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8c7f3586828944be91841ddcdce6c20a
출처 데이터셋
uspto-grants-1978_01
특허 번호
US04071680

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