Pivalaldehyde → HCID 11526594, compound

HRID 251319Notes

Reaction equation

HRID 251319 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 lypholization. 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-6816a2a97f024acfa063b06dfb38a55c
Source dataset
uspto-grants-2011_01
Patent number
US07863333B2

Reaction notes

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