Pyridine → HCID 23532541, compound

HRID 2066049Notes

Reaction equation

HRID 2066049 reaction equation
Cl.C([O:4][C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[C:10](Cl)(=[O:13])[CH2:11][CH3:12].N1C=CC=[CH:17][CH:16]=1>>[CH2:16]([CH2:8][N:7]([C:10](=[O:13])[CH2:11][CH3:12])[CH2:6][C:5]([OH:4])=[O:9])[CH3:17]

Participants

4

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 171173Ethyl N-methylaminoacetate hydrochloride

Product 1

HCID 23532541HCID 23532541, compound

Procedure

A 250 mL round-bottomed flask was charged under a flow of nitrogen with pyridine (50 mL) and sarcosine ethyl ester hydrochloride (25 g) and then placed in an ice bath. Propionyl chloride (14.5 mL) was added by syringe over 15 minutes. After stirring for an additional 20 minutes, the ice bath was removed and the mixture was stirred for one hour. The mixture was poured into cold water (175 mL) and extracted with diethyl ether (2×100 mL) and then ethyl acetate (3×100 mL). The combined extracts were stripped on a rotary evaporator and dried under vacuum, yielding a pale yellow liquid (23.5 g). 1H NMR (CDCl3, 500 MHz) δ4.19 (q, J=7Hz, 2 H), 4.13 (s, 2 H), 3.08 (s, 3 H), 2.82 (q, J=7 Hz, 2 H), 1.29 (t, J=7 Hz, 3 H), 1.15 (t, J=7 Hz, 3 H). GC/MS: >99% pure, m/z=173.

Workup

  1. customplaced in an ice bath
  2. customthe ice bath was removed
  3. stirringthe mixture was stirred for one hour
  4. additionThe mixture was poured into cold water (175 mL)
  5. extractionextracted with diethyl ether (2×100 mL)
  6. customThe combined extracts were stripped on a rotary evaporator
  7. customdried under vacuum

Sources & evidence

ORD record
ord-10f990582a584c918156b038654623e7
Source dataset
uspto-grants-2012_10
Patent number
US08288606B2

Reaction notes

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