Triethyl phosphite → HCID 14557564, compound

HRID 542412Notes

Reaction equation

HRID 542412 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([NH:22][C:23](=[O:25])[CH3:24])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13].[P:26]([O:33]CC)([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29]>>[CH2:28]([O:27][P:26]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([NH:22][C:23](=[O:25])[CH3:24])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])([O:30][CH2:31][CH3:32])=[O:33])[CH3:29]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 13922743HCID 13922743, compound

Product 1

HCID 14557564HCID 14557564, compoundYield 86%

Procedure

A solution of 5 g (1.2 mmol) of ethyl 3-[2-(2-bromoethyl)phenyl]-2-acetamido-2-carboethoxypropanoate in 10 mL of P(OEt)3 was stirred at reflux for 4 h. The excess P(OEt)3 and the volatile by-products were removed from the mixture by distillation under vacuum. The remaining viscous oil was initially purified by column chromatography (C-18, MeOH:H2O; 4:1), then by preparative HPLC (C-18, MeOH:H2O, 7:3) giving 0.48 g (86%) of the product as a clear viscous oil. IR(Nujol) 1745.9, 1676.5 cm-1 (C=O); 1H NMR(CDCl3) δ 1.1-1.5 (m, 12H); 1.8-3.1 (complex, m, 7H); 3.7 (s, 2H); 3.8-4.4 (m, 8H); 6.6 (s, 1H), 7.0-7.3 (m, 4H) Anal. Calcd. for C22H34NO8P: C, 56.04; H, 7.27; N, 2.97. Found: C, 55.91; H, 7.31, N, 2.84.

Workup

  1. temperatureat reflux for 4 h
  2. customThe excess P(OEt)3 and the volatile by-products were removed from the mixture by distillation under vacuum
  3. customThe remaining viscous oil was initially purified by column chromatography (C-18, MeOH:H2O; 4:1)

Sources & evidence

ORD record
ord-f8097c37e3e74faeb4516b1e2e982424
Source dataset
uspto-grants-1987_04
Patent number
US04657899

Reaction notes

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