Trimethylsilyldiazomethane → HCID 67271476, compound

HRID 601721Notes

Reaction equation

HRID 601721 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[C:37]([F:39])[CH:38]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[C:15]([OH:21])[CH:16]=[CH:17][CH:18]=3)[CH2:13][N:12]2[CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:9][C:8](=[O:35])[NH:7]1.[CH3:40][Si](C=[N+]=[N-])(C)C>C(OCC)C.CO>[CH:22]([N:12]1[C@@H:11]([C@H:10]2[O:9][C:8](=[O:35])[NH:7][C@H:6]2[CH2:5][C:4]2[CH:3]=[C:2]([F:1])[CH:38]=[C:37]([F:39])[CH:36]=2)[CH2:20][C:19]2[C:14](=[C:15]([O:21][CH3:40])[CH:16]=[CH:17][CH:18]=2)[CH2:13]1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 67271139HCID 67271139, compound

Product 1

HCID 67271476HCID 67271476, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A 60 mg (0.11 mmol) portion of (4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-2-benzhydryl-8-hydroxy-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one from Step F (14) was dissolved in 2.5 mL of a 4:1 solution of diethyl ether and methanol. A 0.5 mL portion of 2M trimethylsilyldiazomethane was added and the solution was stirred at rt for 16 h. The excess diazomethane was quenched with the addition of several drops of acetic acid and the solvents were removed in vacuo to provide the desired product. 1H NMR (500 MHz, CDCl3) δ ppm 2.45-2.59 (m, 1H) 3.16-3.22 (m, 1H) 3.25 (dd, J=10.07, 5.49 Hz, 1H) 3.67 (s, 3H) 3.76 (s, 1H) 3.80 (d, J=2.14 Hz, 1H) 3.83 (d, J=2.44 Hz, 1H) 3.97-4.03 (m, 1H) 4.08 (d, J=18.62 Hz, 1H) 4.70 (dd, J=10.22, 6.56 Hz, 1H) 4.85 (s, 1H) 4.92 (s, 1H) 6.66 (d, J=7.93 Hz, 1H) 6.78 (d, J=7.63 Hz, 3H) 7.14-7.19 (m, 1H) 7.20-7.29 (m, 5H) 7.32 (t, J=7.63 Hz, 2H) 7.35 (d, J=7.02 Hz, 2H) 7.42 (d, J=7.32 Hz, 2H).

Workup

  1. customThe excess diazomethane was quenched with the addition of several drops of acetic acid
  2. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-c742a45fa26045288dba1b47ec04eb93
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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