Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 11099226, compound

HRID 1675178Notes

Reaction equation

HRID 1675178 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:10]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]([CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:21][CH2:22][CH3:23])=[O:20]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)/[CH:10]=[CH:24]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Product 1

HCID 11099226HCID 11099226, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (S)-(−)-2-(tert-butoxycarbonylamino)-3-phenylpropanal (6.87 g, 27.56 mmol) and (carbethoxymethylene)triphenylphosphine (9.60 g, 27.56 mmol) in toluene (150 mL) was stirred and heated to 80° C. for 70 min. The product was isolated by flash column chromatography on silica gel using a gradient elution of 5-25% EtOAc/hexanes. Collection and concentration of the appropriate fractions yielded the compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.33-7.22 (m, 3H), 7.19-7.17 (m, 2H), 6.92 (dd, J=4.8, 15.6 Hz, 1H), 5.86 (dd, J=1.6, 15.6 Hz, 1H), 4.62 (br s, 1H), 4.52 (br s, 1H), 4.19 (q, J=7.2, 14.0 Hz, 2H), 2.95-2.90 (m, 2H), 1.40 (s, 9H), 1.30-1.25 (m, 3H); ES MS [M-100 (loss of BOC)+1]=220.

Workup

  1. customThe product was isolated by flash column chromatography on silica gel using
  2. washa gradient elution of 5-25% EtOAc/hexanes
  3. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-443417e9769a4b8497b8a234b86579bf
Source dataset
uspto-grants-2011_08
Patent number
US08003653B2

Reaction notes

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