Phosphoethanolamine → Mitomycin phosphate

HRID 1110452

반응식

HRID 1110452 반응식
[P:1]([OH:8])([OH:7])([O:3][CH2:4][CH2:5][NH2:6])=[O:2].C(N(CC)CC)C.[CH3:16][C:17]1[C:23](=[O:24])[C:22]2[N:25]3[C@@:29]([O:36][CH3:37])([C@H:30]([CH2:31][O:32][C:33]([NH2:35])=[O:34])[C:21]=2[C:19](=[O:20])[C:18]=1OC)[C@H:28]1[NH:38][C@H:27]1[CH2:26]3.C(=O)(O)[O-].[Na+]>O.CO>[CH3:16][C:17]1[C:23](=[O:24])[C:22]2[N:25]3[C@@:29]([O:36][CH3:37])([C@H:30]([CH2:31][O:32][C:33]([NH2:35])=[O:34])[C:21]=2[C:19](=[O:20])[C:18]=1[NH:6][CH2:5][CH2:4][O:3][P:1]([OH:8])([OH:7])=[O:2])[C@H:28]1[NH:38][C@H:27]1[CH2:26]3

참가 물질

7

반응물 4

HCID 1015PhosphoethanolamineHCID 8471TriethylamineHCID 19972Mitomycin AHCID 516892Sodium Bicarbonate

생성물 1

HCID 130219Mitomycin phosphate

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of 2-aminoethyl dihydrogen phosphate (56 mg, 0.4 mmol) in water (0.35 ml) and triethylamine (0.3 ml, 2 mmol) was added to mitomycin A (referred to hereinafter as "MMA") (140 mg, 0.4 mmol) in methanol (6 ml) and the reaction was allowed to proceed at room temperature overnight. 1.4 ml of saturated aqueous sodium bicarbonate was then added and the solution was partitioned between water and methylene chloride. The aqueous phase was concentrated to dryness and several portions of methanol were added and evaporated. The residue was taken up into methanol, filtered, and applied to a 2×10 cm C-18 (reverse phase) silica column. The product was eluted with water and all volatile material was evaporated. Methanol was added and evaporated as before and the residue was dried for 24 h under high vacuum in a desiccator with phosphorus pentoxide. The mitomycin phosphate derivative, MOP, was obtained as a fine blue powder (190 mg, 97%).

후처리

  1. customthe solution was partitioned between water and methylene chloride
  2. concentrationThe aqueous phase was concentrated to dryness and several portions of methanol
  3. additionwere added
  4. customevaporated
  5. filtrationfiltered
  6. washThe product was eluted with water
  7. customall volatile material was evaporated
  8. additionMethanol was added
  9. customevaporated as before and the residue
  10. dry with materialwas dried for 24 h under high vacuum in a desiccator with phosphorus pentoxide

출처 및 근거

ORD 기록
ord-292a2b2000f84a3bbef2ad24c573cf89
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04975278

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