Chlorotriethylsilane → HCID 69587097, compound

HRID 1242057Notes

Reaction equation

HRID 1242057 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][OH:18])[O:13][CH2:12][C:11]=2[S:10][C:9]=1[NH2:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20]([O:24][C:25]([C:27]1[C:35]2[CH2:34][CH2:33][O:32][CH:31]([CH2:36][OH:37])[C:30]=2[S:29][C:28]=1[NH2:38])=[O:26])([CH3:23])([CH3:22])[CH3:21].C(N(C(C)C)CC)(C)C.[CH2:48]([Si:50]([CH2:54][CH3:55])([CH2:52][CH3:53])Cl)[CH3:49]>ClCCl>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][O:18][Si:50]([CH2:54][CH3:55])([CH2:52][CH3:53])[CH2:48][CH3:49])[O:13][CH2:12][C:11]=2[S:10][C:9]=1[NH2:19])=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:20]([O:24][C:25]([C:27]1[C:35]2[CH2:34][CH2:33][O:32][CH:31]([CH2:36][O:37][Si:50]([CH2:54][CH3:55])([CH2:52][CH3:53])[CH2:48][CH3:49])[C:30]=2[S:29][C:28]=1[NH2:38])=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 13819ChlorotriethylsilaneHCID 81531DiisopropylethylamineHCID 57275634HCID 57275634, compoundHCID 69585917HCID 69585917, compound

Product 2

HCID 69585691HCID 69585691, compoundYield 16%HCID 69587097HCID 69587097, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of a mixture of 2-amino-5-hydroxymethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester and 2-amino-7-hydroxymethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (1:4 estimated based on 1H NMR) (200 mg, 0.70 mmol) and diisopropylethylamine (0.25 ml, 1.4 mmol) in dichloromethane (6.0 ml) cooled to 0° C. under nitrogen was added triethylchlorosilane (0.18 ml, 1.1 mmol). The solution was stirred at 0° C. for 5 min. and then stirred at room temperature for 15 min. The solution was washed with saturated sodium bicarbonate and brine, dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a 5% mixture of ethyl acetate/hexane as eluant. Pure fractions were collected and the solvent evaporated in vacuo affording 42 mg (16%) of 2-amino-5-triethylsilanyloxymethy-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (1) and 193 mg (69%) of 2-amino-7-triethylsilanyloxymethy-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (2).

Workup

  1. stirringstirred at room temperature for 15 min
  2. washThe solution was washed with saturated sodium bicarbonate and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. customPure fractions were collected
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-8ccb46bbb18b4d7dba6884c9914a46c3
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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