Cyano-borohydride → HCID 67126832, compound

HRID 574914Notes

Reaction equation

HRID 574914 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1([F:16])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[O:21]1[CH2:24][C:23](=O)[CH2:22]1.C([BH3-])#N>O1CCCC1.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:17]([NH2:20])(=[O:18])=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1([F:16])[CH2:15][CH2:14][N:13]([CH:23]2[CH2:24][O:21][CH2:22]2)[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 498716Cyano-borohydrideHCID 150242543-OxetanoneHCID 67126678HCID 67126678, compound

Product 1

HCID 67126832HCID 67126832, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 322C (830 mg) in tetrahydrofuran (15 mL) and acetic acid (5 mL) was added oxetan-3-one (163 mg) and MP-cyanoborohydride (2.38 mmol/g, 1.9 g). The mixture was stirred at room temperature overnight. The reaction was then filtered and the filtrate was concentrated under vacuum. The residue was slurried in ether and the solid product was collected by filtration.

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. filtrationthe solid product was collected by filtration

Sources & evidence

ORD record
ord-7a6a233155fe4a73bc473cbe3a1d9878
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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