Hydrochloric Acid → HCID 57971602, compound

HRID 2360662Notes

Reaction equation

HRID 2360662 reaction equation
[CH:1]1([O:6][C:7](=[O:33])[C@@H:8]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][NH:25]C(OC(C)(C)C)=O)=[CH:20][CH:19]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.O1CCOCC1>>[CH:1]1([O:6][C:7](=[O:33])[C@@H:8]([NH:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][NH2:25])=[CH:22][CH:23]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57971739HCID 57971739, compound

Product 1

HCID 57971602HCID 57971602, compoundYield 79%

Procedure

(S)-2-[4-(tert-Butoxycarbonylamino-methyl)-benzylamino]-3-phenyl-propionic acid cyclopentyl ester was treated with 4M HCl in dioxane (1 mL, 0.25 mmol) and stirred at r.t. for 1 h. The mixture was evaporated to dryness and partitioned between EtOAc (20 mL) and water (20 mL). Saturated sodium bicarbonate (20 mL) was added to the aqueous layer which was then extracted with EtOAc (3×20 mL). The organic layers were combined, dried (Na2SO4) and evaporated to dryness to give the desired product (263 mg, 79% over 2 steps). m/z 353 [M++H]+

Workup

  1. customThe mixture was evaporated to dryness
  2. custompartitioned between EtOAc (20 mL) and water (20 mL)
  3. additionSaturated sodium bicarbonate (20 mL) was added to the aqueous layer which
  4. extractionwas then extracted with EtOAc (3×20 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-914f824bb2df47c8ae060361396fb6c7
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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