Sodium triacetoxyborohydride → HCID 178502916, compound

HRID 1614900Notes

Reaction equation

HRID 1614900 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([N:9]([C:19]2[CH:23]=[C:22]([C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27])[S:21][C:20]=2[C:30]([OH:32])=[O:31])[C:10]([CH:12]2[CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH2:13]2)=[O:11])[CH2:5][CH2:4]1.[CH3:33][O:34][P:35]1(=[O:42])[CH2:40][CH2:39][C:38](=O)[CH2:37][CH2:36]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:29][C:26]([CH3:27])([CH3:28])[C:25]#[C:24][C:22]1[S:21][C:20]([C:30]([OH:32])=[O:31])=[C:19]([N:9]([CH:6]2[CH2:5][CH2:4][CH:3]([NH:2][CH:38]3[CH2:39][CH2:40][P:35]([O:34][CH3:33])(=[O:42])[CH2:36][CH2:37]3)[CH2:8][CH2:7]2)[C:10]([C@H:12]2[CH2:13][CH2:14][C@H:15]([CH3:18])[CH2:16][CH2:17]2)=[O:11])[CH:23]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 110737321-Methoxyphosphinan-4-one 1-oxideHCID 67036200HCID 67036200, compound

Product 1

HCID 178502916HCID 178502916, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(N-(4-aminocyclohexyl)-4-methylcyclohexanecarboxamido)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid hydrochloride (40 mg, 0.083 mmol) and 1-methoxy-1-oxo-1λ5-phosphinan-4-one (27 mg, 0.166 mmol) were dissolved in 2 mL of DMF. Sodium triacetoxyborohydride (35 mg, 0.166 mmol) was added. The reaction mixture was allowed to stir at room temperature over 18 hours, and then diluted with EtOAc, washed with saturated sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified by HPLC (Gemini column; 5% acetonitrile:water, 5 min; 5-100% acetonitrile:water, 18 min; 100% acetonitrile, 6 min; both solvents containing 0.1% trifluoroacetic acid) to give title compound (38.6 mg): MS (m/z): 591.3 [M+H]−; HPLC retention time: 3.28 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Workup

  1. washwashed with saturated sodium bicarbonate and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC (Gemini column
  6. customwater, 5 min
  7. customwater, 18 min
  8. custom100% acetonitrile, 6 min
  9. additionboth solvents containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-13e78af9ec5a4cca8d6f0a45ebc06eb7
Source dataset
uspto-grants-2014_07
Patent number
US08765722B2

Reaction notes

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