Trimethylsilyldiazomethane → HCID 86603426, compound

HRID 1028609Notes

Reaction equation

HRID 1028609 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Si:8]([O:15][C@H:16]([C:30]1[NH:34][N:33]=[N:32][N:31]=1)[C@@H:17]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:18])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>C(Cl)Cl.CO>[Si:8]([O:15][C@H:16]([C:30]1[N:34]([CH3:1])[N:33]=[N:32][N:31]=1)[C@@H:17]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:18])([C:11]([CH3:13])([CH3:14])[CH3:12])([CH3:9])[CH3:10].[Si:8]([O:15][C@H:16]([C:30]1[N:31]=[N:32][N:33]([CH3:1])[N:34]=1)[C@@H:17]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:18])([C:11]([CH3:13])([CH3:14])[CH3:12])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 86603428HCID 86603428, compoundHCID 178462185HCID 178462185, compound

Product 2

HCID 86603426HCID 86603426, compoundHCID 86603427HCID 86603427, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

(Trimethylsilyl)diazomethane (2M in hexanes, 459 μL, 0.918 mmol) was added dropwise to a solution of the crude benzyl [(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methyl-2-(1H-tetrazol-5-yl)ethyl]carbamate and benzyl [(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methyl-2-(2H-tetrazol-5-yl)ethyl]carbamate in CH2Cl2/MeOH (3:2, 5 mL) at room temperature under N2. After 15 min and gas evolution had ceased, the reaction mixture was concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-70% EtOAc in hexanes gradient) to afford benzyl [(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methyl-2-(1-methyl-1H-tetrazol-5-yl)ethyl]carbamate and benzyl [(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methyl-2-(2-methyl-2H-tetrazol-5-yl)ethyl]carbamate, as a 2:1 mixture of regioisomers. LCMS calc.=406.2; found=406.2 (M+1)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto give the crude product
  3. customThis was purified by flash chromatography (Si, 12×160 mm, 0-70% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-2c53d1b5a50c42a99040617bdd545630
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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