Hydrochloric Acid → (S)-tert-butyl 2-(2-aminobutoxy)acetate

HRID 2204987Notes

Reaction equation

HRID 2204987 reaction equation
C(OC([NH:8][C@@H:9]([CH2:20][CH3:21])[CH2:10][O:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:8][C@@H:9]([CH2:20][CH3:21])[CH2:10][O:11][CH2:12][C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 86678281(S)-tert-butyl 2-(2-(tert-butoxycarbonylamino)butoxy)acetate

Product 1

HCID 87385354(S)-tert-butyl 2-(2-aminobutoxy)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 2-(2-(tert-butoxycarbonylamino)butoxy)acetate (1 eq, from the previous step) in DCM (0.4 M) at room temperature was added a solution of 4 M HCl in dioxane (10 eq). The reaction was stirred for 2 hours, at which time more 4 M HCl in dioxane (3 eq) was added and stirred for 1 hour. The reaction mixture was concentrated en vaccuo to give the product as an oil. The material was carried onto the next step without further purification.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated en vaccuo

Sources & evidence

ORD record
ord-29982f93124d4af4997245f0abfa0b43
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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