Citric Acid → HCID 178495743, 화합물

HRID 1629855노트

반응식

HRID 1629855 반응식
CCCCC(F)(F)C(O)CC[C@@H:9]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]CC(O)=O)[C:12](=[O:13])C[C@H]1O.C1C[CH2:32][CH:31]([NH:34]C2CCCCC2)[CH2:30]C1.[C:41]([NH:48][C@H:49](C(O)=O)[CH2:50][O:51][CH3:52])([O:43]C(C)(C)C)=O.[Br:56][C:57]1[CH:62]=[CH:61][C:60]([NH2:63])=[C:59]([NH2:64])[CH:58]=1.C(N(CC)CC)C.C(O)(=O)C[C:74](CC(O)=O)(C(O)=O)[OH:75]>C1COCC1.C(OCC)(=O)C.O>[Br:56][C:57]1[CH:62]=[CH:61][C:60]2[NH:63][C:30]([C@@H:31]([NH:34][C:12](=[O:13])[C:14]3[CH:15]=[CH:16][C:17]([N:48]4[CH2:49][CH2:50][O:51][CH2:52][C:41]4=[O:43])=[C:18]([CH3:19])[CH:9]=3)[CH2:32][O:75][CH3:74])=[N:64][C:59]=2[CH:58]=1

참가 물질

9

반응물 5

HCID 311Citric AcidHCID 8471TriethylamineHCID 3235934-Bromobenzene-1,2-diamineHCID 7016354(2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acidHCID 7174909515-Hydroxy Lubiprostone Dicyclohexylammonium Salt

생성물 1

HCID 178495743HCID 178495743, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

2.50 g (6.24 mmol) of the dicyclohexylammonium salt of N-Boc-(S)-O-methyl-serine are dissolved in 20 ml 5% citric acid, the aqueous phase is extracted 2× with 20 ml of ethyl acetate, the combined organic phases are dried over sodium sulphate and freed from solvent i. vac. The residue is dissolved together with 1.23 g (6.55 mmol) 4-bromo-1,2-phenylenediamine in 30 ml THF and 1.42 ml (14.0 mmol) triethylamine and 4.97 ml (7.80 mmol) of a 50% solution of PPA in ethyl acetate are added with stirring in the ice bath. After 5 minutes stirring in the ice bath the mixture is heated to ambient temperature and stirred for 23 hours at ambient temperature. The reaction mixture is poured into 100 ml of water and the aqueous phase is extracted with ethyl acetate. The combined organic phases are extracted with sat. sodium carbonate solution and water, dried over sodium sulphate and evaporated down i. vac.

후처리

  1. extractionthe aqueous phase is extracted 2× with 20 ml of ethyl acetate
  2. dry with materialthe combined organic phases are dried over sodium sulphate
  3. additionare added
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. extractionThe combined organic phases are extracted with sat. sodium carbonate solution and water
  6. dry with materialdried over sodium sulphate
  7. customevaporated down i

출처 및 근거

ORD 기록
ord-8ecb60d0e6cb435aa125eddc587b8186
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791103B2

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