Diazomethane → HCID 53637764, compound

HRID 986728Notes

Reaction equation

HRID 986728 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([P:14]([OH:16])[OH:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:19])=[N-]>CCOCC>[CH3:19][O:16][P:14]([CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:13])[OH:15]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 19880129HCID 19880129, compound

Product 1

HCID 53637764HCID 53637764, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Benzyloxycarbonylaminoethylphosphonous acid, prepared by the method of E. K. Baylis et al. [J. Chem. Soc., Perkin Trans, 2845-2853 (1984)] was esterified with diazomethane in an ether solution prepared by a method of F. Arndt [Organic Syn. Coll. V. II 165-167 (1943)]. The compound was purified by standard chromatography on silica gel. TLC (silica, 9:1, ethyl acetate:acetonitrile) Rf =0.51 NMR (CDCl3, TMS) δ 1.2 and 1.5 (2d, 3H); 2.2 and 10.1 (d, 1H); 3.6 (d, 3H); 3.9 (m, 1H); 5.0 (s, 2H); 6.0-6.6 (overlapping doublets, 1H); 7.2 (s, 5H).

Workup

  1. customprepared by a method of F
  2. customThe compound was purified by standard chromatography on silica gel

Sources & evidence

ORD record
ord-330435df9b0e483eb7a9b0db57be38a2
Source dataset
uspto-grants-1987_12
Patent number
US04715994

Reaction notes

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