Hydrochloric Acid → N-(2-BOC-Aminoethyl)-N-(uracil-5-ylacetyl)glycine

HRID 1281079Notes

Reaction equation

HRID 1281079 reaction equation
[C:1]([CH:8]([NH2:28])[CH2:9][N:10]([C:17](=[O:27])[CH2:18][C:19]1[C:20](=[O:26])[NH:21][C:22](=[O:25])[NH:23][CH:24]=1)[CH2:11][C:12]([O:14]CC)=[O:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl>[OH-].[Na+]>[C:1]([CH:8]([NH2:28])[CH2:9][N:10]([C:17](=[O:27])[CH2:18][C:19]1[C:20](=[O:26])[NH:21][C:22](=[O:25])[NH:23][CH:24]=1)[CH2:11][C:12]([OH:14])=[O:13])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69352349HCID 69352349, compound

Product 1

HCID 56976930N-(2-BOC-Aminoethyl)-N-(uracil-5-ylacetyl)glycineYield 100.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl N-(2-BOC-aminoethyl)-N-(uracil-5-ylacetyl)glycinate (35, 1.00 g, 2.5 mmol) was dissolved in 1 M aqueous sodium hydroxide (50 ml) and the mixture was stirred for 15 min at room temperature. The reaction mixture was cooled to 0° C. and the pH was adjusted to 1.5 by the addition of 2 M hydrochloric acid. After 30 min the aqueous solution was extracted with n-butanol (4×80 ml). The n-butanol of the combined organic phases was evaporated under reduced pressure. Residual n-butanol was removed azeotropically with water (5×50 ml). The resultant aqueous solution was freeze-dried to yield 0.93 g (100%) of the title compound as a white solid. Due to hindered rotation around the amide bond several of the NMR signals are comprised of a major (ma) and minor (mi) component. 1H-NMR (DMSO-d6/TMS): δ=1.44 (s, 9H, BOC); 3.07-3.48 (m, CH2CON, NCH2, CH2N and water); 4.00 (ma), 4.26 (mi) (s, 2H, CH2COO); 6.75 (mi), 6.94 (ma) (br, 1H, BOC-NH); 7.28 (mi), 7.32 (ma) (d, 1H, J=5.5 Hz, H-6); 10.87 (br, 1H, H-1); 11.12 (br, 1H, H-3). MS (FAB+) m/z (%): 371 (26, M+H). Calcd. for C15H22N4O7: C, 48.65; H, 5.99; N, 15.13; C/N, 3.22. Found: C, 35.13; H, 4.66; N, 10.48; C/N, 3.35.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionAfter 30 min the aqueous solution was extracted with n-butanol (4×80 ml)
  3. customThe n-butanol of the combined organic phases was evaporated under reduced pressure
  4. customResidual n-butanol was removed azeotropically with water (5×50 ml)
  5. customThe resultant aqueous solution was freeze-dried

Sources & evidence

ORD record
ord-1747be2a4efb4faea1bc89799f3e9d11
Source dataset
uspto-grants-2002_09
Patent number
US06451968B1

Reaction notes

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