Diazomethane → HCID 57779521, compound

HRID 509203Notes

Reaction equation

HRID 509203 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([OH:20])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:29])=[N-]>C1COCC1>[CH3:29][O:19][C:18](=[O:20])[CH:17]([CH:14]1[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12][CH2:13]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 17781827HCID 17781827, compound

Product 1

HCID 57779521HCID 57779521, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of compound 90 (1.281 g, 3.62 mmol) in THF (40 mL) was added an excess of diazomethane at room temperature and the reaction mixture was stirred for 15 minutes. Nitrogen was bubbled into the reaction mixture for 15 minutes then it was concentrated to afford compound 91 (1.032 g, 77%) as a colorless oil after purification by ISCO (0 to 50% EtOAc in hexanes). LRMS (ESI): (calc) 367.44 (found) 368.16 (MH)+. 1H NMR (CD3OD-d4) δ (ppm):7.33-7.23 (m, 10H), 5.09 (s, 2H), 4.18-4.14 (m, 1H), 4.05-4.01 (m, 1H), 3.63 (s, 3H), 3.33-3.30 (m, 1H), 2.86-2.72 (m, 2H), 2.21 (qt, J=11.3, 3.5 Hz, 1H), 1.78 (d, J=12.7 Hz, 1H), 1.28-1.18 (m, 2H), 0.96 (qd, J=12.5, 4.3 Hz, 1H).

Workup

  1. customNitrogen was bubbled into the reaction mixture for 15 minutes
  2. concentrationit was concentrated

Sources & evidence

ORD record
ord-53e3400905ed4773955004b550758659
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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