Pyridine → N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

HRID 1682432Notes

Reaction equation

HRID 1682432 reaction equation
[CH3:1][O:2][C:3](=[O:8])[C@H:4]([CH2:6][OH:7])[NH2:5].N1C=CC=CC=1.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:8])[C@H:4]([CH2:6][OH:7])[NH:5][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 10387Benzyl chloroformateHCID 2723731(S)-methyl 2-amino-3-hydroxypropanoate

Product 1

HCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

Mix L-serine methyl ester (6.6 mmol) and pyridine (60 mL). Add, by dropwise addition, benzyl chloroformate (7.3 mmol) and stir overnight. Remove excess pyridine in vacuo and dissolve the residue in a two-phase mixture of ethyl acetate/water. Separate the organic phase and extract the aqueous phase with additional ethyl acetate (2×). Wash the combined organic phases with water, then brine and dry (MgSO4). Evaporate the solvent in vacuo to give N -(benzyloxycarbonyl)-L-serine methyl ester.

Workup

  1. customSeparate the organic phase
  2. extractionextract the aqueous phase with additional ethyl acetate (2×)
  3. washWash the combined organic phases with water
  4. dry with materialbrine and dry (MgSO4)
  5. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-402cd6130bfa4ec28dfba31a1c1c6ee4
Source dataset
uspto-grants-1997_06
Patent number
US05635502

Reaction notes

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