Potassium Carbonate → HCID 86723200, compound

HRID 1050317Notes

Reaction equation

HRID 1050317 reaction equation
[N+](C1C=CC(C([O:10][C@@H:11]2[CH2:28][N:14]3[C:15](=[O:27])[CH2:16][CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][C@@H:13]3[CH2:12]2)=O)=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CO>CO>[OH:10][C@@H:11]1[CH2:28][N:14]2[C:15](=[O:27])[CH2:16][CH2:17][N:18]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:19][C@@H:13]2[CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21584119Ethylacetate methanolHCID 86723199HCID 86723199, compound

Product 1

HCID 86723200HCID 86723200, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To tert-butyl (8S,9aS)-8-[(4-nitrobenzoyl)oxy]-5-oxohexahydro-1H-pyrrolo[1,2-a][1,4]diazepine-2(3H)-carboxylate (495 mg, 0.291 mmol, Part A) in methanol (8 ml) was added potassium carbonate (98 mg, 0.708 mmol). The mixture was stirred at room temperature for one hour, and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate, then ethyl acetate/methanol=10:1) to give 280 mg (88% yield) of the title compound as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (s, 9H), 1.61 (m, 1H), 2.24 (m, 1H), 2.38 (m, 1H), 2.58 (m, 1H), 2.80-3.15 (m, 2H), 3.23 (dd, J=13, 4 Hz, 1H), 3.42 (dd, J=13, 4 Hz, 1H), 3.81 (m, 1H), 3.98 (m, 2H), 4.18 (m, 1H), 5.02 (t, J=4 Hz, 1H); MS (ESI) m/z 271.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-21e74f856c8a4933ba36a842aa1c8606
Source dataset
uspto-grants-2016_07
Patent number
US09382258B2

Reaction notes

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