Citric Acid → HCID 178495743, compound

HRID 2222508Notes

Reaction equation

HRID 2222508 reaction equation
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

Participants

9

Reactant 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

Product 1

HCID 178495743HCID 178495743, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b8f8d0dfa34446d88458351e8b8ca8be
Source dataset
uspto-grants-2008_05
Patent number
US07371743B2

Reaction notes

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