Formic Acid → HCID 86713018, compound

HRID 711308Notes

Reaction equation

HRID 711308 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9](=[O:22])[CH:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][C:12]#[CH:13].N12CCN(CC1)CC2.C(O)=O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]([OH:22])[C@@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:11][C:12]#[CH:13]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 9237DabcoHCID 577886571,1-Dimethylethyl N-[1-(2,5-difluorobenzoyl)-3-butyn-1-yl]carbamate

Product 1

HCID 86713018HCID 86713018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred vessel under nitrogen sweep was charged tert-butyl [1-(2,5-difluorophenyl)-1-oxopent-4-yn-2-yl]carbamate (35.0 kg, 113 mol), 1,4-diazabicyclo[2.2.2]octane (38.0 kg, 339 mol), and THF (465 kg). After dissolution, chloro{[(1R,2R)-(+2-amino-1,2-diphenylethyl](pentafluorophenylsulfonyl)amido}-(p-cymene) ruthenium (II) (410 g, 576 mmol) was added. The vessel was vacuum sparged and back-filled with nitrogen three times. Then, formic acid (26.7 kg, 580 mol) was added and the reaction heated to 45° C. overnight.

Workup

  1. dissolutionAfter dissolution, chloro{[(1R,2R)-(+2-amino-1,2-diphenylethyl](pentafluorophenylsulfonyl)amido}-(p-cymene) ruthenium (II) (410 g, 576 mmol)
  2. additionwas added
  3. customsparged
  4. additionback-filled with nitrogen three times

Sources & evidence

ORD record
ord-19dc3d703a51432687fb3a5e80439f78
Source dataset
uspto-grants-2015_11
Patent number
US09181262B2

Reaction notes

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