Triethylamine → HCID 131726650, compound

HRID 1182095Notes

Reaction equation

HRID 1182095 reaction equation
Cl.[F:2][C:3]1[CH:14]=[CH:13][C:6]([C:7](N2CCC2)=[O:8])=[CH:5][CH:4]=1.[CH2:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])C.[C:22]([O:26][C:27](=[O:52])[NH:28][C@H:29]([C:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[O:34][SiH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])CCI)([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O>[C:22]([O:26][C:27](=[O:52])[NH:28][C@H:29]([C:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[O:34][SiH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:21][CH2:20][N:17]1[CH2:15][CH:19]([C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([F:2])=[CH:14][CH:13]=2)[CH2:18]1)([CH3:23])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69410956HCID 69410956, compoundHCID 131726651HCID 131726651, compound

Product 1

HCID 131726650HCID 131726650, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-fluorobenzoyl-azetidine hydrochloride (0.192 g, 0.892 mmol), triethylamine (0.252 ml, 3.24 mmol) and [(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-iodo-propyl]-carbamic acid tert-butyl ester (0.448 g, 0.811 mmol) in dimethylformamide (3 ml) is stirred at ambient temperature for 18 hours, then partitioned between ethylacetate and water. The ethylacetate phase is dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution with a 1:99 methanol/dichloromethane) to afford {(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-[3-(4-fluoro-benzoyl)-azetidin-1-yl]-propyl}carbamic acid tert-butyl ester. [MH]+ 605.2.

Workup

  1. custompartitioned between ethylacetate and water
  2. dry with materialThe ethylacetate phase is dried over MgSO4
  3. customevaporated
  4. customThe crude product is purified by flash silica chromatography (
  5. washelution with a 1:99 methanol/dichloromethane)

Sources & evidence

ORD record
ord-a347f5e56bcc47d8bfc822db4552cdee
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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