Hydrochloric Acid → HCID 57971602, compound

HRID 2277007Notes

Reaction equation

HRID 2277007 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-b9c68acd06cb4e8290bf9c13b62c990b
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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