Pivalaldehyde → HCID 11526594, compound

HRID 2250802Notes

Reaction equation

HRID 2250802 reaction equation
[NH2:1][CH2:2][C@H:3]([NH:9][C:10]([CH2:12][NH:13][C:14]([C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[NH:26][C:27]([N:29]1[CH2:32][CH2:31][CH2:30]1)=[O:28])=[O:15])=[O:11])[C@@H:4]([OH:8])[CH2:5][CH2:6][CH3:7].[CH3:33][C:34]([CH3:38])([CH3:37])[CH:35]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:33][C:34]([CH3:38])([CH3:37])[CH2:35][NH:1][CH2:2][C@H:3]([NH:9][C:10]([CH2:12][NH:13][C:14]([C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[NH:26][C:27]([N:29]1[CH2:32][CH2:31][CH2:30]1)=[O:28])=[O:15])=[O:11])[C@@H:4]([OH:8])[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 90735272HCID 90735272, compound

Product 1

HCID 11526594HCID 11526594, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Azetidine-1-carboxylic acid (1S,2S)-(2-{[(1-aminomethyl-2-hydroxy-pentylcarbamoyl)-methyl]-carbamoyl}-4-trifluoromethyl-phenyl)-amide (165 mg, 0.35 mmol, see procedure 1b) was dissolved in dichloroethane (4 mL). The resultant solution was charged sequentially with trimethylacetaldehyde (20.5 mg, 0.2 mmol) and sodium triacetoxyborohydride (148 mg, 0.7 mmol), stirred for 3 h at RT, quenched with sat. NaHCO3, and extracted twice with EtOAc. The organic extracts were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by reverse-phase HPLC to afford the title compound (55 mg) as a white powder after lyopholization. MS found: (M+H)+=530.5.

Workup

  1. customquenched with sat. NaHCO3
  2. extractionextracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-1ec43e545b784e4dbdc35631ff1ae92a
Source dataset
uspto-grants-2008_01
Patent number
US07317019B2

Reaction notes

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