Ammonia → HCID 178457107, 화합물

HRID 347900

반응식

HRID 347900 반응식
[CH3:1][N:2]([C@@H:4]1[C:27](=[O:28])[C:26]([C:29]([NH2:31])=[O:30])=[C:25]([OH:32])[C@:24]2([OH:33])[C@H:5]1[CH2:6][C@H:7]1[C:21]([C:22]2=[O:23])=[C:20]([OH:34])[C:10]2[C:11]([OH:19])=[C:12]([NH2:18])[CH:13]=[C:14]([N:15]([CH3:17])[CH3:16])[C:9]=2[CH2:8]1)[CH3:3].ClCC(OC)(OC)OC.Cl[CH2:45][C:46]1O[C:48]2[CH:54]=CC=C[C:49]=2[N:50]=1.C(N)CC.C(NCC1OC2C=CC=CC=2N=1)CC.N>CN(C=O)C>[CH3:17][N:15]([CH3:16])[C:14]1[C:9]2[CH2:8][C@@H:7]3[C:21](=[C:22]([OH:23])[C@@:24]4([OH:33])[C@@H:5]([CH2:6]3)[C@H:4]([N:2]([CH3:1])[CH3:3])[C:27]([OH:28])=[C:26]([C:29]([NH2:31])=[O:30])[C:25]4=[O:32])[C:20](=[O:34])[C:10]=2[C:11]2[O:19][C:45]([CH2:46][NH:50][CH2:49][CH2:48][CH3:54])=[N:18][C:12]=2[CH:13]=1

참가 물질

8

반응물 6

HCID 222AmmoniaHCID 7852PropylamineHCID 1447021,1,1-Trimethoxy-2-chloroethaneHCID 20619892-(Chloromethyl)-1,3-benzoxazoleHCID 546761129-AminominocyclineHCID 60677375n-Propylaminomethyl benzoxazole

생성물 1

HCID 178457107HCID 178457107, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

9-aminominocycline sulfate salt (1.0 g, 1.50 mmol) is dissolved in DMF (50 mL) and treated with a solution of 2-chloro-1,1,1-trimethoxyethane (0.463 g, 3.00 mmol, 2 equivalents). The reaction is stirred at room temperature until mass spectrometry shows conversion to the chloromethylbenzoxazole derivative. The solution is then treated with n-propylamine (10 mL, excess) and stirred until mass spectrometry shows conversion to the n-propylaminomethyl benzoxazole. The mixture is concentrated under reduced pressure to remove excess n-propylamine, and then poured slowly into ether (1 L) and HCl/ether is added to precipate the salt. The solid is rinsed with fresh ether and dried under vacuum. The crude solid is dissolved in water (100 mL) giving a solution at pH 2. The pH is raised successively by 0.5 units with aqueous ammonia, and extracted with dichloromethane. The fractions extracted at pH 4–4.5 are combined, dried (Na2SO4), filtered and concentrated nearly to dryness. A small volume of methanol is added and the solution is treated with 1M HCl in ether. The precipitated solid is collected by filtration, washed with fresh ether and dried under vacuum to yield 0.067 g of the product as its HCl salt.

후처리

  1. stirringstirred until mass spectrometry
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove excess n-propylamine
  4. additionpoured slowly into ether (1 L) and HCl/ether
  5. additionis added
  6. washThe solid is rinsed with fresh ether
  7. customdried under vacuum
  8. dissolutionThe crude solid is dissolved in water (100 mL)
  9. customgiving a solution at pH 2
  10. extractionextracted with dichloromethane
  11. extractionThe fractions extracted at pH 4–4.5
  12. dry with materialdried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated nearly to dryness
  15. additionA small volume of methanol is added
  16. additionthe solution is treated with 1M HCl in ether
  17. filtrationThe precipitated solid is collected by filtration
  18. washwashed with fresh ether
  19. customdried under vacuum

출처 및 근거

ORD 기록
ord-4335d33fec944396a3c54b10160f8090
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176225B2

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