Potassium tert-butoxide → HCID 86723201, compound

HRID 1050318Notes

Reaction equation

HRID 1050318 reaction equation
[OH:1][C@@H:2]1[CH2:19][N:5]2[C:6](=[O:18])[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C@@H:4]2[CH2:3]1.Br[C:21]1[CH:26]=[N:25][C:24]([CH:27]2[CH2:29][CH2:28]2)=[CH:23][N:22]=1.CC(C)([O-])C.[K+]>O1CCCC1.ClCCl>[CH:27]1([C:24]2[N:25]=[CH:26][C:21]([O:1][C@@H:2]3[CH2:19][N:5]4[C:6](=[O:18])[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:10][C@@H:4]4[CH2:3]3)=[N:22][CH:23]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 457876352-Bromo-5-cyclopropylpyrazineHCID 86723200HCID 86723200, compound

Product 1

HCID 86723201HCID 86723201, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl (8S,9aS)-8-hydroxy-5-oxohexahydro-1H-pyrrolo[1,2-a][1,4]diazepine-2(3H)-carboxylate (270 mg, 1 mmol, Part B) and 2-bromo-5-cyclopropylpyrazine (299 mg, 1.5 mmol) in tetrahydrofuran (3 mL) and dichloromethane (1 mL) was added potassium t-butoxide (3 mL, 3 mmol, 1 M in tetrahydrofuran). The mixture was stirred at room temperature for three days, and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate) to give 255 mg (65.6% yield) of the title compound as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 0.98 (m, 4H), 1.47 (s, 9H), 2.01 (m, 2H), 2.61 (m, 3H), 3.01 (m, 2H), 3.80-3.98 (m, 3H), 4.22 (m, 2H), 5.40 (m, 1H), 7.95 (d, J=1 Hz, 1H), 8.02 (d, J=1 Hz, 1H); MS (ESI) m/z 389.0 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-b3ecb01640d040bf90d1ce927cc1794b
Source dataset
uspto-grants-2016_07
Patent number
US09382258B2

Reaction notes

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