Methyl chloroformate → (S)-2-(Methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid

HRID 2203134Notes

Reaction equation

HRID 2203134 reaction equation
[NH2:1][C@@H:2]([CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4].C(=O)(O)[O-].[Na+].Cl[C:18]([O:20][CH3:21])=[O:19]>Cl>[CH3:21][O:20][C:18]([NH:1][C@@H:2]([CH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1)[C:3]([OH:5])=[O:4])=[O:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 1512541(S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetic acid

Product 1

HCID 59264488(S)-2-(Methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (S)-amino-(tetrahydro-pyran-4-yl)-acetic acid (1 g, 6.28 mmol) in saturated aqueous sodium bicarbonate solution (12.32 mL, 125.6 mmol) was stirred until all solids were dissolved. Methyl chloroformate (0.97 mL, 12.56 mmol) was added dropwise, the reaction mixture was stirred for 1 h, and IN HCl was added to adjust pH to 1. The reaction mixture was extracted with ethyl acetate (3×15 mL) and the organic extracts were dried over sodium sulfate, filtered, concentrated and dried overnight under vacuum to give the title intermediate (1.36 g, 99% yield) as a white, sticky solid. (m/z): [M+H]+ calcd for C9H15NO5 218.10 found 218.3.

Workup

  1. dissolutionwere dissolved
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×15 mL)
  3. dry with materialthe organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried overnight under vacuum

Sources & evidence

ORD record
ord-47a170b932204ece87c5c88b09c8970c
Source dataset
uspto-grants-2016_06
Patent number
US09365549B2

Reaction notes

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