Sodium triacetoxyborohydride → HCID 66832616, compound

HRID 579552Notes

Reaction equation

HRID 579552 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]=O.Cl.[C:13]([NH:16][C:17]([CH2:38][CH2:39][CH2:40][NH2:41])([CH2:25][CH2:26][CH2:27][CH2:28][B:29]1[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]1)[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(=[O:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:13]([NH:16][C:17]([CH2:38][CH2:39][CH2:40][NH:41][CH2:10][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])([CH2:25][CH2:26][CH2:27][CH2:28][B:29]1[O:30][C:31]([CH3:37])([CH3:36])[C:32]([CH3:35])([CH3:34])[O:33]1)[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 15948879(2,4-Dichlorophenyl)acetaldehydeHCID 66833217HCID 66833217, compound

Product 1

HCID 66832616HCID 66832616, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (2,4-dichlorophenyl)acetaldehyde (0.8 mmol) and 2-acetamido-2-(3-aminopropyl)-N-tert-butyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide hydrochloride (260 mg, 0.58 mmol) in dichloromethane (5 mL) was stirred at room temperature. After 30 min, sodium triacetoxyborohydride (310 mg, 1.45 mmol) was added in one portion and stirring was continued overnight. Once complete, the solution was diluted with dichloromethane (10 mL), quenched with aq 5% NaHCO3 (W/V, 5 mL) and stirred vigorously for 30 min. The layers were separated and the organic phase was washed with water and sat'd aq sodium chloride, dried over MgSO4, filtered and concentrated. Purification by flash column chromatography (1-20% methanol in dichloromethane) gave 2-acetamido-N-tert-butyl-2-(3-(2,4-dichlorophenethylamino)propyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (140 mg, 47%). ESI MS found for C29H48BCl2N3O4 m/z [584.6/586.6 (M+1)].

Workup

  1. waitwas continued overnight
  2. customquenched with aq 5% NaHCO3 (W/V, 5 mL)
  3. stirringstirred vigorously for 30 min
  4. customThe layers were separated
  5. washthe organic phase was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography (1-20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a4276b86f17046c9a3f72d6a5546b4e6
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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