Hydrochloric Acid → 3-Amino-propionic acid dipropylcarbamoylmethyl ester

HRID 386706Notes

Reaction equation

HRID 386706 reaction equation
[CH2:1]([N:4]([CH2:21][CH2:22][CH3:23])[C:5]([CH2:7][O:8][C:9](=[O:20])[CH2:10][CH2:11][NH:12]C(OC(C)(C)C)=O)=[O:6])[CH2:2][CH3:3].Cl>O1CCOCC1>[CH2:21]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([CH2:7][O:8][C:9](=[O:20])[CH2:10][CH2:11][NH2:12])=[O:6])[CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86663348HCID 86663348, compound

Product 1

HCID 866633473-Amino-propionic acid dipropylcarbamoylmethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a cooled stirred solution of 3-tert-butoxycarbonylamino-propionic acid dipropylcarbamoylmethyl ester (step 1) (36.5 g, 110 mmol) in dry dioxane under N2 was added dropwise 4N HCl in dioxane (18.12 ml, 597 mmol). The resulting mixture was allowed to warm to RT and stirred overnight. The solvent was removed in vacuo and the crude product was suspended in EtOAc (500 ml) and sonicated for 1 h. The resulting white precipitate was isolated by filtration and was dried under vacuum at 40° C. for 1 h to afford a pale yellow solid. Recrystallisation from EtOAc afforded the title compound; LC-MS Rt 0.77 mins; 231.2 [M+H]+, Method 2minLC_v003.

Workup

  1. customThe solvent was removed in vacuo
  2. customsonicated for 1 h
  3. customThe resulting white precipitate was isolated by filtration
  4. customwas dried under vacuum at 40° C. for 1 h
  5. customto afford a pale yellow solid
  6. customRecrystallisation from EtOAc

Sources & evidence

ORD record
ord-0ff57614030e4b7a8f8ebb3f6a2016d9
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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