Hydrochloric Acid → HCID 68561906, compound

HRID 20478Notes

Reaction equation

HRID 20478 reaction equation
C([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:40])[C@@H:15]([NH:25][C:26](=[O:39])/[C:27](/[CH3:38])=[CH:28]/[C:29](=[O:37])[N:30]([CH2:34][CH2:35][CH3:36])[CH2:31][CH2:32][CH3:33])[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:12][O:11][C@@H:10]([O:41][CH2:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH2:9]1)=[O:7])(C)(C)C.[ClH:49].C(OCC)C>FC(F)(F)C(O)=O.ClCCl>[ClH:49].[CH:43]1([CH2:42][O:41][C@@H:10]2[O:11][CH2:12][C@H:13]([C@@H:14]([OH:40])[C@@H:15]([NH:25][C:26](=[O:39])/[C:27](/[CH3:38])=[CH:28]/[C:29](=[O:37])[N:30]([CH2:31][CH2:32][CH3:33])[CH2:34][CH2:35][CH3:36])[CH2:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[N:8]([C:6]([OH:7])=[O:5])[CH2:9]2)[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68558045HCID 68558045, compound

Product 1

HCID 68561906HCID 68561906, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve (2R,5R)-2-cyclohexylmethoxy-5-[(1S,2S)-3-(3,5-difluorophenyl)-2-((E)-3-dipropylcarbamoyl-2-methylacryloylamino)-1-hydroxypropyl]-morpholine-4-carboxylic acid tert-butyl ester (0.051 g, 0.075 mmol) in trifluoroacetic acid (1.5 mL) and stir at room temperature for 15 minutes. Dilute with dichloromethane (15 mL), concentrate, dissolve in ethyl acetate (30 mL), wash with 1:1 saturated aqueous sodium chloride:saturated aqueous sodium bicarbonate (30 mL), dry (sodium sulfate) and concentrate. Dissolve the residue in ethyl acetate and add 1 M hydrogen chloride in diethyl ether (0.20 mL, 0.20 mmol) and concentrate to give the title compound (0.045 g, 97.3%).

Workup

  1. concentrationconcentrate
  2. dissolutiondissolve in ethyl acetate (30 mL)
  3. washwash with 1:1 saturated aqueous sodium chloride
  4. dry with materialsaturated aqueous sodium bicarbonate (30 mL), dry (sodium sulfate)
  5. concentrationconcentrate
  6. dissolutionDissolve the residue in ethyl acetate
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-08ccfc082ec442ff9a7e76686e15b50e
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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