4-Methylmorpholine → HCID 17878856, compound

HRID 1354526Notes

Reaction equation

HRID 1354526 reaction equation
[C:1]([N:8]([CH2:10][C:11]([OH:13])=O)[CH3:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.Cl.[CH3:22][O:23][C:24](=[O:27])[CH2:25][NH2:26]>C(Cl)Cl>[CH3:22][O:23][C:24](=[O:27])[CH2:25][NH:26][C:11](=[O:13])[CH2:10][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:9]

Participants

5

Reactant 3

HCID 79724-Methylmorpholine2×HCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 17878856HCID 17878856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a suspension of Boc-sarcosine (9.0 g, 048 mol) in 70 ml of CH2Cl2 at −20° C. was added isobutyl chlorofomate (7.1 g, 0.052 mol) and N-Methylmorpholine (4.8 g, 0.047 mol). After 2 min glycine methyl ester, hydrochloride (7.19g, 0.057 mol) and N-methylmorpholine (5.76g, 0.057 mol) in CH2Cl2 (60 ml) was added. The reaction was stirred at −10° C. for 1 h and allowed to warm to room temperature. After 4h at room temperature, the reaction was filtered and washed with salt. NaHCO3 (100 ml), 1N NaHCO3 100 ml, twice with 1N KHSO4 (100 ml), water (100 ml) and brine (70 ml). The organic phase was dried with Na2SO4 and evaporated. The yield of Boc sarcosyl-glycine methyl ester was 89%.

Workup

  1. temperatureto warm to room temperature
  2. filtrationAfter 4h at room temperature, the reaction was filtered
  3. washwashed with salt
  4. dry with materialThe organic phase was dried with Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-8cb42ead2aa7404797641370cce7c174
Source dataset
uspto-grants-2007_05
Patent number
US07223833B1

Reaction notes

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