Acetic Acid → HCID 86722647, compound

HRID 1480414Notes

Reaction equation

HRID 1480414 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][CH:12]=O)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[N:14]1([C:20]([O:22][CH2:23][C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=2)=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:5]([O:4][C:3]([N:2]([CH3:1])[CH2:10][CH2:11][CH2:12][N:17]1[CH2:16][CH2:15][N:14]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=2)=[O:21])[CH2:19][CH2:18]1)=[O:9])([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 10442454tert-butyl N-methyl-N-(3-oxopropyl)carbamateHCID 59474105HCID 59474105, compound

Product 1

HCID 86722647HCID 86722647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl methyl(3-oxopropyl)carbamate (step 3) (1.528 g, 8.16 mmol) was solubilised in DCM (50 ml) and added to 3,5-dichlorobenzyl piperazine-1-carboxylate (step 2) (3.09 g, 9.82 mmol). The resulting mixture was treated with acetic acid (56 μl, 0.982 mmol) and after stirring for 1 hr at RT, sodium triacetoxyborohydride (4.16 g, 19.64 mmol) was added. The reaction mixture was stirred at RT overnight and then quenched by addition of 2M NaOH (aq.). The aqueous layer was basified to pH 14 with conc NaOH solution. The organic layer was separated and the aqueous layer was extracted with more DCM. The organic portions were combined, dried over MgSO4 (anh), filtered and evaporated under reduced pressure, yielding a yellow oil. The crude product was purified by chromatography on silica eluting with 0-10% MeOH (with ammonia) in DCM to afford the title compound;

Workup

  1. stirringThe reaction mixture was stirred at RT overnight
  2. customquenched by addition of 2M NaOH (aq.)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with more DCM
  5. dry with materialdried over MgSO4 (anh)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customyielding a yellow oil
  9. customThe crude product was purified by chromatography on silica eluting with 0-10% MeOH (with ammonia) in DCM

Sources & evidence

ORD record
ord-34ccd8a2c7924891942e5a37c4d0ec15
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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