Gamma-Aminobutyric Acid → 4-(((Tert-butoxy)carbonyl)amino)butanoic acid

HRID 722704Notes

Reaction equation

HRID 722704 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].C(N(CC)CC)C.[CH3:15][C:16]([O:19][C:20](ON=C(C1C=CC=CC=1)C#N)=[O:21])([CH3:18])[CH3:17]>O1CCOCC1>[C:16]([O:19][C:20]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:21])([CH3:18])([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidYield 51.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
-20 °C

Procedure

Prepared as described for L2 from stirring 4-aminobutyric acid (3.94 g, 38.2 mmol) in 50% aqueous dioxane with triethylamine (8.0 mL, 57 mmol) and BOC-ON (10.4 g, 42.2 mmol). A yellow oil was obtained that solidified upon addition of hexanes and cooling to −20° C. to yield a cream solid (4.03 g, 51.8%). 1H NMR (d6-DMSO, 300 MHz): δ 1.36 (s, 9H, CH3), 1.57 (m, 2H, CH2), 2.17 (t, 2H, CH2), 2.90 (m, 2H, CH2), 6.80 (t, 1H, NH).

Workup

  1. customPrepared
  2. customA yellow oil was obtained

Sources & evidence

ORD record
ord-857235fb301d41cc90f7ae607cb3878d
Source dataset
uspto-grants-2006_11
Patent number
US07138520B2

Reaction notes

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