Hydrochloric Acid → HCID 57971602, compound

HRID 548265Notes

Reaction equation

HRID 548265 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-1f6b0ea797d6458796056ee6e75b7179
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

Loading…