Dichloromethane → HCID 15550129, compound

HRID 1383564Notes

Reaction equation

HRID 1383564 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:10].[C:25](Cl)(=[O:41])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].C(Cl)Cl>O1CCCC1>[C:25]([NH:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:10])(=[O:41])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8206Palmitoyl chlorideHCID 517045Sodium AcetateHCID 18792877HCID 18792877, compound

Product 1

HCID 15550129HCID 15550129, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium acetate (50% in water, 29 ml) was added in three portions to a stirred solution of 2-amino-4′-benzyloxyacetophenone HCl (4.6 g, 17 mmol) and tetrahydrofuran (200 ml). Palmitoyl chloride (19 mmol) in tetrahydrofuran (25 ml) was added dropwise over 20 min yielding a dark brown solution. The mixture was stirred overnight at room temperature. The aqueous fraction was removed by use of a separatory funnel and chloroform/methanol (2/1, 150 ml) was added to the organic layer which was then washed with water (50 ml). The yellow aqueous layer was extracted once with chloroform (50 ml). The organic solutions were then pooled and rotoevaporated until near dryness. The residue was redissolved in chloroform (100 ml) and crystallized by the addition of hexane (400 ml). The flask was cooled to 4° C. for 2 h. The crystals were filtered and washed with cold hexane and dried in a fume hood overnight. The product yield was 3.79 g (8 mmol). An Rf of 0.21 was observed when resolved by thin layer chromatography using methylene chloride. [M+H]+: 479 for C31H45NO3. 1H nmr (δ, ppm, CDCl3), 7.96 (2H, δ, 8.8 Hz, O—Ar—C(O)), 7.40 (5H, m, Ar′CH2O—), 7.03 (2H, δ, 8.8 Hz, O—Ar—C(O)), 6.57 (1H, bs, NH2), 5.14 (2H, s, Ar′CH2O—), 4.71 (2H, s, C(O)CH2NHC(O)), 2.29 (2H, t, 7.4 Hz, C(O)CH2(CH2)13CH3), 1.67 (2H, m, C(O)CH2(CH2)13CH3), 0.87 (3H, t, 6.7 Hz, C(O)CH2(CH2)13CH3).

Workup

  1. customyielding a dark brown solution
  2. customThe aqueous fraction was removed by use of a separatory funnel
  3. additionchloroform/methanol (2/1, 150 ml) was added to the organic layer which
  4. washwas then washed with water (50 ml)
  5. extractionThe yellow aqueous layer was extracted once with chloroform (50 ml)
  6. dissolutionThe residue was redissolved in chloroform (100 ml)
  7. customcrystallized by the addition of hexane (400 ml)
  8. temperatureThe flask was cooled to 4° C. for 2 h
  9. filtrationThe crystals were filtered
  10. washwashed with cold hexane
  11. customdried in a fume hood overnight

Sources & evidence

ORD record
ord-160c973359044a44b750cd95b842eb3d
Source dataset
uspto-grants-2001_07
Patent number
US06255336B1

Reaction notes

Loading…