Chloroacetic Acid → HCID 18964105, compound

HRID 2226986Notes

Reaction equation

HRID 2226986 reaction equation
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].Cl[CH2:8][C:9]([OH:11])=[O:10].[OH-].[Na+]>O>[OH:4][CH2:3][CH:2]([CH2:5][OH:6])[NH:1][CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 14798Sodium HydroxideHCID 68294Serinol

Product 1

HCID 18964105HCID 18964105, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Serinol (2.5 g, 26 mMol), chloroacetic acid (2.41 g, 26 mMol) and NaOH (3.2 ml 10N, 52 mMol) were dissolved in 25 ml water and stirred at room temperature for 16 h. The solution was concentrated on a rotoevaporator, and the resulting glass was redissolved in methanol. Addition of acetone gave a white solid (2 g, 51%) which was recrystallised from methanol/ethyl acetate. Mass spec calculated for C5H11NO4 : 149; found: 150 (M+1); 1H NMR in D2O (0.75% TMS): 3.85 (m, 4H), 3.80 (s, 2H), 3.45 (m, 1H).

Workup

  1. concentrationThe solution was concentrated on a rotoevaporator
  2. dissolutionthe resulting glass was redissolved in methanol
  3. additionAddition of acetone

Sources & evidence

ORD record
ord-8aa3c6d5958a47deac9d7dcc0bee7c1f
Source dataset
uspto-grants-1994_09
Patent number
US05350837

Reaction notes

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