Beta-Alanine → N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

HRID 722703Notes

Reaction equation

HRID 722703 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[CH3:14][C:15]([O:18][C:19](ON=C(C1C=CC=CC=1)C#N)=[O:20])([CH3:17])[CH3:16]>O1CCOCC1.O.C(OCC)(=O)C>[C:15]([O:18][C:19]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:20])([CH3:17])([CH3:16])[CH3:14]

Participants

7

Reactant 3

HCID 239Beta-AlanineHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineYield 64.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Triethylamine (6.2 mL, 45 mmol) was added to a solution of 3-aminopropionic acid (2.67 g, 30.0 mmol) in 50% aqueous dioxane (30 mL). BOC-ON (8.15 g, 33.1 mmol) was added and the reaction stirred for 3 h at room temperature. The reaction solution was diluted with H2O (40 mL) and ethyl acetate (60 mL). The aqueous layer was isolated, washed with ethyl acetate, and acidified with a 5% citric acid solution. The aqueous layer was subsequently extracted with ethyl acetate. The organic fractions were combined and evaporated to yield L2 as a cream solid (3.64 g, 62.8%). 1H NMR (d6-DMSO, 300 MHz): δ 1.35 (s, 9H, CH3), 2.33 (t, 2H, CH2), 3.11 (q, 2H, CH2), 6.67 (t, 1H, NH).

Workup

  1. customThe aqueous layer was isolated
  2. washwashed with ethyl acetate
  3. extractionThe aqueous layer was subsequently extracted with ethyl acetate
  4. customevaporated

Sources & evidence

ORD record
ord-d47c51d2c502442d81e9f265dcc89623
Source dataset
uspto-grants-2006_11
Patent number
US07138520B2

Reaction notes

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