Hydrochloric Acid → HCID 45380613, compound

HRID 468038Notes

Reaction equation

HRID 468038 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C@H:10]([OH:40])[CH2:11][CH2:12][C@H:13]1[C@H:17]([OH:18])[CH2:16][C@H:15]([OH:19])[C@@H:14]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]C(=O)[C@H](CCCNC(=N)N)N)=[O:27].[Cl-].[NH4+].Cl.[Cl-].[Na+]>CO.O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C@H:10]([OH:40])[CH2:11][CH2:12][C@H:13]1[C@H:17]([OH:18])[CH2:16][C@H:15]([OH:19])[C@@H:14]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 25517Ammonium ChlorideHCID 178512920HCID 178512920, compound

Product 1

HCID 45380613HCID 45380613, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To 1.0 gram of Arginyl 7-((1R,2R,3R,5S)-2-((R)-4-(2-fluorophenylthio)-3-hydroxybutyl)-3,5-dihydroxy cyclopentyl)heptanoate (8) in MeOH/H2O (4:1, 20 mL) is added, dropwise with cooling, at least 5 equivalents of a 3:1 mixture of saturated aqueous ammonium chloride and 1 M hydrochloric acid (Sigma-Aldrich, St. Louis, Mo.), and the solution is stirred for 15 minutes. Saturated aqueous sodium chloride is added along with ethyl acetate. The organic layer is separated; is washed again with brine; the solvents removed in vaccuo, and the material chromatographed to give the free acid, 7-((1R,2R,3R,5S)-2-((R)-4-(2-fluorophenylthio)-3-hydroxybutyl)-3,5-dihydroxy cyclopentyl)heptanoic acid (9).

Workup

  1. temperaturedropwise with cooling
  2. customThe organic layer is separated
  3. washis washed again with brine
  4. customthe solvents removed in vaccuo
  5. customthe material chromatographed

Sources & evidence

ORD record
ord-a27842e0b7034d7d86e6269eca9e5328
Source dataset
uspto-grants-2014_01
Patent number
US08623918B2

Reaction notes

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