Sarcosine → HCID 131713406, compound

HRID 1388752Notes

Reaction equation

HRID 1388752 reaction equation
[CH3:1][C:2]([CH3:13])([O:4][C:5]([NH:7][C@H:8]([C:10]([OH:12])=O)[CH3:9])=[O:6])[CH3:3].CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[CH3:30][NH:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].CNCC(O)=O>C(OCC)(=O)C.CCCCCC.C(Cl)(Cl)Cl>[CH3:13][C:2]([CH3:1])([O:4][C:5]([NH:7][C@H:8]([C:10]([N:31]([CH3:30])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:12])[CH3:9])=[O:6])[CH3:3]

Participants

8

Reactant 5

HCID 1088SarcosineHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 85082Tert-butoxycarbonylalanineHCID 171173Ethyl N-methylaminoacetate hydrochloride

Product 1

HCID 131713406HCID 131713406, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of N-[(1,1-dimethylethoxy)-carbonyl]-L-alanine (2.48 g., 13.1 mmole) and dry chloroform (20 ml.) at -20° under argon is treated with N-methylmorpholine (1.47 ml., 1.0 eq.) and isobutylchloroformate (1.8 ml., 1.0 eq.) and stirred for 20 minutes. N-Methylglycine, ethyl ester, hydrochloride (2.0 g., 1.0 eq.) and N-methyl morpholine (1.47 ml.) are added. After one hour, the ice-bath is removed and the reaction mixture is stirred for an additional 3 hours. The mixture is then partitioned between ethyl acetate/5% potassium bisulfate, and the organic phase is washed with 5% potassium bisulfate, saturated sodium bicarbonate, dried (Na2SO4), and evaporated to give 3.7 g. of crude N-[N-(1,1-dimethylethoxy)carbonyl]-L-alanyl]-N-methylglycine, ether ester as an oil. Tlc (ethyl acetate/hexane, 1:2) shows a major spot at Rf =0.22.

Workup

  1. waitAfter one hour
  2. customthe ice-bath is removed
  3. stirringthe reaction mixture is stirred for an additional 3 hours
  4. customThe mixture is then partitioned between ethyl acetate/5% potassium bisulfate
  5. washthe organic phase is washed with 5% potassium bisulfate, saturated sodium bicarbonate
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give 3.7 g

Sources & evidence

ORD record
ord-30d5d736b34149f2a167ca91310796d2
Source dataset
uspto-grants-1984_02
Patent number
US04432971

Reaction notes

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