Glycolic Acid → HCID 90408187, compound

HRID 594035Notes

Reaction equation

HRID 594035 reaction equation
[NH2:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[OH:16][CH2:17][C:18](O)=[O:19].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[OH:19][CH2:18][C:17]([NH:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)=[O:16]

Participants

6

Reactant 3

HCID 757Glycolic AcidHCID 1515269(R)-2-Aminomethyl-4-Boc-morpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 90408187HCID 90408187, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-tert-butyl 2-(aminomethyl)morpholine-4-carboxylate (1.0 equiv.), 2-hydroxyacetic acid (1.80 equiv.), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (2.0 equiv.), and N,N-dimethylpyridin-4-amine (0.20 equiv.) was stirred in DCM (0.1 M) at room temperature overnight. The reaction was quenched with water and washed (3×) with water. The combined aqueous fractions were then back-extracted with chloroform (4×) and the combined organics were dried over Na2SO4, filtered, and concentrated. The resulting oil was passed through a pad of SiO2 gel using 5-50% MeOH/DCM and concentrated to yield (R)-tert-butyl 2-((2-hydroxyacetamido)methyl)morpholine-4-carboxylate as an oil. LCMS (m/z) (M+H)=175.1 (-Boc), Rt=0.55 min.

Workup

  1. customThe reaction was quenched with water
  2. washwashed (3×) with water
  3. extractionThe combined aqueous fractions were then back-extracted with chloroform (4×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a658fbc37aff43ed85c82aa00876eee5
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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