Hydrochloric Acid → HCID 67497525, compound

HRID 1628260Notes

Reaction equation

HRID 1628260 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:26]C(=O)OC(C)(C)C)[C:10](=[O:25])[NH:11][C:12]2[C:13](=[O:24])[NH:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH:17]=2)[CH:5]=[CH:6][CH:7]=1.Cl>C(Cl)Cl>[NH2:26][C@@H:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:10]([NH:11][C:12]1[C:13](=[O:24])[NH:14][CH:15]=[C:16]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[CH:17]=1)=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67496879HCID 67496879, compound

Product 1

HCID 67497525HCID 67497525, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 25.1.C was stirred in DCM with HCl (4.0 M, dioxane) until the deprotection was complete. The reaction mixture was concentrated to a solid and partitioned with saturated NaHCO3(aq)/CHCl3:IPA (4:1). The aqueous layer was further extracted (2×) and the organics were combined, dried with sodium sulfate, filtered, and concentrated to give a light tan solid (230 mg, 47%).

Workup

  1. concentrationThe reaction mixture was concentrated to a solid
  2. custompartitioned with saturated NaHCO3(aq)/CHCl3:IPA (4:1)
  3. extractionThe aqueous layer was further extracted (2×)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b351400b97384e3291d3770ec391cd9a
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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