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Imidazole → tert-Butyl(2S)-2-{[tert-butyl-(dimethyl)silyl]oxy}-3-phenoxypropyl{[(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl}carbamate

HRID 47680
Notes
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Reaction equation

HRID 47680 reaction equation
[OH:1][C@H:2]([CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][N:4]([CH2:12][C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([I:23])[CH:19]=2)[O:14]1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].N1C=CN=C1.O>CN(C=O)C>[Si:32]([O:1][C@H:2]([CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][N:4]([CH2:12][C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([I:23])[CH:19]=2)[O:14]1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:8])[CH3:9])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 86587738HCID 86587738, compound

Product 1

HCID 86587739tert-Butyl(2S)-2-{[tert-butyl-(dimethyl)silyl]oxy}-3-phenoxypropyl{[(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl}carbamateYield 97%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
27 °C

Procedure

A reaction mixture containing tert-butyl (2S)-2-hydroxy-3-phenoxypropyl{[(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl}carbamate (Example 81, 8.625 mmol, 1.0 eq.), tert-butyldimethylsilyl chloride (10.35 mmol, 1.2 eq.), and imidazole (21.5625 mmol, 2.5 eq.) in anhydrous DMF (18 mL) was stirred at 27° C. overnight. The resulting mixture was then cooled to room temperature, poured into water, and extracted with diethyl ether. The organic extract was washed with water, brine, dried over anhydrous sodium sulfate, concentrated, and purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, hexanes:EtOAc=100:5). The product was obtained as a colorless oil in 97% yield. MH+=654.0, retention time (LC-MS)=5.29 min.

Workup

  1. temperatureThe resulting mixture was then cooled to room temperature
  2. extractionextracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, hexanes:EtOAc=100:5)
  8. customThe product was obtained as a colorless oil in 97% yield

Sources & evidence

ORD record
ord-9f3de52e00c14c16b241f0b983454b1a
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06699860B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes