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Chemical Structure| 13515-93-0 Chemical Structure| 13515-93-0
Chemical Structure| 13515-93-0

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Synonyms: Methyl N-methylglycinate hydrochloride

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Product Details of H-Sar-OMe.HCl

CAS No. :13515-93-0
Formula : C4H10ClNO2
M.W : 139.58
SMILES Code : O=C(OC)CNC.[H]Cl
Synonyms :
Methyl N-methylglycinate hydrochloride
MDL No. :MFCD00038876
InChI Key :HQZMRJBVCVYVQA-UHFFFAOYSA-N
Pubchem ID :83544

Safety of H-Sar-OMe.HCl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of H-Sar-OMe.HCl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 13515-93-0 ]
  • Downstream synthetic route of [ 13515-93-0 ]

[ 13515-93-0 ] Synthesis Path-Upstream   1~2

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YieldReaction ConditionsOperation in experiment
90% With triethylamine In dichloromethane at 0 - 20℃; for 48 h; Inert atmosphere To a suspension of sarcosine (35.64 g, 0.40 mol) in 350 mL MeOH was added thionyl chloride (29.02 mL, 0.40 mol) dropwise at 0 °C. After complete addition the cooling bath was removed and the reaction mixture was stirred for 30 min at r.t. and refluxed for further 6 h. The resulting solution was concentrated in vacuum and the residue was dried in high vacuum over night at r.t. to afford sarcosine methyl ester.HCl as a white powder which was used in the next step without further purification; yield: 56.14 g (quant.); mp. 102 °C. 1H-NMR (300 MHz, CDCl3): δ = 9.76 (s, 2 H, NH2), 3.88 (t, J = 5.6 Hz, 2 H, H-2), 3.82 (s, 3 H, H-4)), 2.83 (t, J = 5.2 Hz, 3 H, H-3). 13C-NMR(75 MHz, CDCl3): δ = 166.7 (C-1), 53.3 (C-2), 48.9 (C-3), 33.4 (C-4).1 To a suspension of sarcosine methylester.HCl (59.80 g, 0.43 mol) and (Boc)2O (138.01 mL, 0.65 mol) in 1.0 L CH2Cl2 TEA (119.09 mL, 0.86 mol) was added dropwise at 0 °C. After complete addition the cooling bath was removed and the reaction mixture was stirred for two days at r.t. Aq. HCl (1 M) was added until the aqueous layer showed pH = 6. The resulting two layers were separated and the organic layer was washed with dist. H2O, dried (Na2SO4), concentrated in vacuum and volatile impurities were removed in high vacuum over night at r.t. to afford a clear oil; yield: 78.65 g (90 percent)
References: [1] Synthesis (Germany), 2017, vol. 49, # 4, p. 770 - 774.
[2] Patent: EP1032561, 2004, B1, . Location in patent: Page 21.
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References: [1] Gazzetta Chimica Italiana, 1977, vol. 107, p. 381 - 385.
 

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