Dichloromethane → Diethyl 3-chloro-4-aminobenzylphosphonate

HRID 964632Notes

Reaction equation

HRID 964632 reaction equation
Cl[C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:3]=1[C:4](O)=O.B#B.[P:16]([O:23]CC)([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19].C(Cl)[Cl:27]>C1COCC1.C1COCC1.O>[Cl:27][C:10]1[CH:2]=[C:3]([CH:7]=[CH:8][C:9]=1[NH2:11])[CH2:4][P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 74482-Chloro-4-nitrobenzoic acidHCID 31215Triethyl phosphiteHCID 6328200Diboron

Product 1

HCID 19077629Diethyl 3-chloro-4-aminobenzylphosphonate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with diethyl 3-chloro-4-aminobenzylphosphonate to generate the title compound. The diethyl 3-chloro-4-aminobenzylphosphonate was prepared from commercial 2-chloro-4-nitrobenzoic acid upon sequential treatment with 1) diborane in THF; 2) φ3P,CBr4 in CH2Cl2 ; 3) P(OEt)3 at 125° C.; and 4) reduction with Na2S2 O4 in THF/H2O at 100° C.

Workup

  1. customat 125° C.
  2. customat 100° C.

Sources & evidence

ORD record
ord-d525ce8277e245ed9b248400d6fb59a2
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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