Benzyl chloroformate → (2R,3S)-N-carbobenzyloxy-beta-phenyl isoserine methyl ester

HRID 1739445Notes

Reaction equation

HRID 1739445 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([OH:13])[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:6].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C@H:4]([OH:13])[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH:6][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

6

Reactant 2

HCID 10387Benzyl chloroformateHCID 10176516(2R,3S)-3-Phenylisoserine methyl ester

Product 1

HCID 22865499(2R,3S)-N-carbobenzyloxy-beta-phenyl isoserine methyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2R,3S)-β-phenyl isoserine methyl ester (2) (Preparation 1, 2 mM) in pyridine containing a small amount of DMAP is cooled in an ice bath and treated with benzyl chloroformate (0.8 ml). After stirring at room temperature overnight, the reaction is diluted with ethyl acetate, washed with 5% aqueous sodium bisulfate, dried and evaporated. The product is obtained pure by silica gel chromatography in ethyl acetate-hexane mixtures. Mp 120-121° C. NMR(CDCl3, TMS): δ3.26 (m, 1H); 3.79 (s, 3H); 4.47 (m, 1H); 5.06 (m, 2H); 5.27 (d, 1H); 5.75 (m, 1H); 7.20-7.50 (m, 10 H).

Workup

  1. washwashed with 5% aqueous sodium bisulfate
  2. customdried
  3. customevaporated
  4. customThe product is obtained pure by silica gel chromatography in ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-8cdc3bb31283470097d63ac4194387a2
Source dataset
uspto-grants-1999_10
Patent number
US05965739

Reaction notes

Loading…