Boron Trichloride → HCID 22405474, compound

HRID 441208Notes

Reaction equation

HRID 441208 reaction equation
[CH3:1][C:2]1([CH2:8][O:9][C:10]([NH:12][C:13]2[C:14](=[O:39])[N:15]([CH2:25][C:26]([NH:28][CH:29]([CH:36]([CH3:38])[CH3:37])[C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[O:27])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[O:11])[CH2:7][O:6]C[O:4][CH2:3]1.B(Cl)(Cl)Cl>C(Cl)Cl>[OH:6][CH2:7][C:2]([CH2:3][OH:4])([CH3:1])[CH2:8][O:9][C:10]([NH:12][C:13]1[C:14](=[O:39])[N:15]([CH2:25][C:26]([NH:28][CH:29]([CH:36]([CH3:38])[CH3:37])[C:30](=[O:35])[C:31]([F:33])([F:34])[F:32])=[O:27])[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:17][CH:18]=1)=[O:11]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 53785829HCID 53785829, compound

Product 1

HCID 22405474HCID 22405474, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[3-(5-methyl-1,3-dioxacyclohex-5-ylmethoxy-carbonylamino)-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.35 g) in methylene chloride (6 mL), cooled to 0° C. , was added dropwise 1.27 mL of a 10M methylene chloride solution of boron trichloride, and the reaction mixture allowed to warm to room temperature over 30 min. The reaction mixture was quenched by pouring into 25 mL of a 15% aqueous sodium chloride solution and stirring 15 min. Ethyl acetate (10 mL) was added, and the organic phase washed with brine, dried (MgSO4) and evaporated. Chromatography, using as eluant methylene chloride:methanol (20:1), followed by overnight vacuum-drying (50° C. at 27 Pa) yielded the title compound as a white solid (0.25 g); mp 94°-97° C. (dec); TLC: Rf =0.11, dichloromethane:methanol (95:5); 300 MHz NMR: 0.80 (s,3), 0.85 (s,3), 2.15 (m,1), 3.32 (2d,4), 3.98 (s,2), 4.4-4.6 (m,4), 4.65 (t,]), 6.25 (dd,1), 7.43 (m,5), 7.90 (d,1), 8.40 (d,1), 8.75 (d,1); IR(KBr): 3400 (broad), 2980, 1700, 1650, 1600, 1525, 1215 cm-1 ; MS: m/z=542(M+1).

Workup

  1. customThe reaction mixture was quenched
  2. additionby pouring into 25 mL of a 15% aqueous sodium chloride solution
  3. additionEthyl acetate (10 mL) was added
  4. washthe organic phase washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. waitfollowed by overnight
  8. customvacuum-drying (50° C. at 27 Pa)

Sources & evidence

ORD record
ord-173e19d0213d4b3e92ce842ec3671ac3
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

Loading…