Sodium Hydroxide → N-(N'-Boc-aminoethyl)-N-[(1-thyminyl)propanoyl]glycine

HRID 1166444Notes

Reaction equation

HRID 1166444 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][N:6]([CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:7](=[O:19])[CH2:8][CH2:9][N:10]1[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[NH:13][C:11]1=[O:12])C.[OH-].[Na+]>CO>[C:23]([NH:22][CH2:21][CH2:20][N:6]([C:7](=[O:19])[CH2:8][CH2:9][N:10]1[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[NH:13][C:11]1=[O:12])[CH2:5][C:4]([OH:30])=[O:3])([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86595832N-(N'-BOC-aminoethyl)-N-[(1-thyminyl)-propanoyl]glycine ethyl ester

Product 1

HCID 67297594N-(N'-Boc-aminoethyl)-N-[(1-thyminyl)propanoyl]glycine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(N′-BOC-aminoethyl)-N-[(1-thyminyl)propanoyl]glycine ethyl ester (0.83 g, 0.00195 mol) was dissolved in methanol (25 mL). Sodium hydroxide (2 M, 25 mL) was added. The solution was stirred for 1 h. The methanol was removed by evaporation in vacuo, and the pH adjusted to 2 with 4 M hydrochloric acid at 0° C. The product was isolated by filtration, washed with ether (3×15 mL), and dried over sicapent, in vacuo. Yield: 0.769 g, 99%). M.p. 213° C. (decomp.).

Workup

  1. customThe methanol was removed by evaporation in vacuo
  2. customadjusted to 2 with 4 M hydrochloric acid at 0° C
  3. customThe product was isolated by filtration
  4. washwashed with ether (3×15 mL)
  5. customdried over sicapent, in vacuo

Sources & evidence

ORD record
ord-77ef1f8c14b34d719a0fb6ea6d294542
Source dataset
uspto-grants-2003_09
Patent number
US06613873B1

Reaction notes

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