Sarcosine → Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-

HRID 1388750Notes

Reaction equation

HRID 1388750 reaction equation
[NH:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2].C(N(CC)CC)C.[C:14]([O:18][C:19]([O:21]N=C(C1C=CC=CC=1)C#N)=O)([CH3:17])([CH3:16])[CH3:15]>O1CCOCC1.O>[CH3:17][C:14]([CH3:15])([O:18][C:19]([N:1]([CH3:2])[CH2:3][C:4]([OH:6])=[O:5])=[O:21])[CH3:16]

Participants

6

Reactant 3

HCID 1088SarcosineHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of sarcosine (1.5 g., 16.7 mmole), triethylamine (3.5 ml., 1 eq.), and water (10 ml.) is treated with 2-(t-butyoxycarbonyloxyimino)-2-phenylacetonitrile (4.5 g., 1.1 eq.) in dioxane (10 ml.) at 25°. After 3 hours, the reaction mixture is diluted with water and then washed twice with ethyl acetate. The aqueous phase is acidified to pH 3.0 with 10% citric acid and the resulting oil is extracted with ethyl acetate (twice). The combined extracts are washed with brine, dried (MgSO4), and evaporated to give 3.0 g. of N-[(1,1-dimethylethoxy)carbonyl]-N-methylglycine as a viscous oil which crystallizes on standing; m.p. 84°-85.5°. Tlc (dichloromethane/methanol/acetic acid; 100:5:5) shows a single spot at Rf 0.6.

Workup

  1. washwashed twice with ethyl acetate
  2. extractionthe resulting oil is extracted with ethyl acetate (twice)
  3. washThe combined extracts are washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give 3.0 g
  7. customof N-[(1,1-dimethylethoxy)carbonyl]-N-methylglycine as a viscous oil which crystallizes on standing

Sources & evidence

ORD record
ord-1da4bbc04fee4aec98cb07ac0bc67e8a
Source dataset
uspto-grants-1984_02
Patent number
US04432971

Reaction notes

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