Hydrochloric Acid → N-Boc-L-serine methyl ester

HRID 1452395Notes

Reaction equation

HRID 1452395 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O.Cl>CO>[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH:6][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 7019177N-Boc-L-serine methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of serine methyl ester hydrochloride (0.12 g, 0.78 mmol) in 1.6 ml of dry MeOH, at room temperature, under argon, were added successively triethylamine (10% solution, 0.16 ml) and (BOC)2O (0.19 g, 1.1 eq.) and the solution was stirred for 60 minutes. It was then poured in cold 2% HCl and the aqueous layer was extracted with CH2Cl2 (3×). The combined organic extracts were dried over MgSO4, the solids were filtered and the solvents evaporated to give 0.17 g (100%) of the titled compound as a clear oil.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationthe solids were filtered
  4. customthe solvents evaporated

Sources & evidence

ORD record
ord-16acef04a5704d5489131e4ef7fd1397
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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