Imidazole → (S)-tert-Butyl 2-((S)-1-amino-3-(4-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxo-2,3-dihydrobenzo[d]thiazol-6-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate

HRID 600334Notes

Reaction equation

HRID 600334 reaction equation
[NH2:1][C:2](=[O:40])[C@@H:3]([NH:24][C:25]([C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:23]=[CH:22][C:14]3[N:15]([CH2:19][CH2:20][OH:21])[C:16](=[O:18])[S:17][C:13]=3[CH:12]=2)=[CH:7][CH:6]=1.[Si:41](Cl)([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42].N1C=CN=C1.O>CN(C=O)C>[NH2:1][C:2](=[O:40])[C@@H:3]([NH:24][C:25]([C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]1[C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])=[O:26])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:23]=[CH:22][C:14]3[N:15]([CH2:19][CH2:20][O:21][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[C:16](=[O:18])[S:17][C:13]=3[CH:12]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride2×HCID 57999687(S)-tert-Butyl 2-((S)-1-amino-3-(4-(3-(2-hydroxyethyl)-2-oxo-2,3-dihydrobenzo[d]thiazol-6-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 57999684(S)-tert-Butyl 2-((S)-1-amino-3-(4-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxo-2,3-dihydrobenzo[d]thiazol-6-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylateYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-tert-butyl 2-((S)-1-amino-3-(4-(3-(2-hydroxyethyl)-2-oxo-2,3-dihydrobenzo[d]thiazol-6-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate (138 mg), tert-butyldimethylsilyl chloride (40.2 mg) and imidazole (41.3 mg) in DMF (1 mL) was stirred for 16 h. Further tert-butyldimethylsilyl chloride (40.2 mg) and imidazole (41.3 mg) were added and stirred for 4 h. Water was added and the mixture was extracted thrice with ethyl acetate. The organic layers were washed twice with water, combined, dried over magnesium sulfate, evaporated and purified by flash silica chromatography eluting with 1:2 acetone/isohexane to give the subtitle compound (130 mg) as a colourless gum.

Workup

  1. extractionthe mixture was extracted thrice with ethyl acetate
  2. washThe organic layers were washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. custompurified by flash silica chromatography
  6. washeluting with 1:2 acetone/isohexane

Sources & evidence

ORD record
ord-6777d666f37d4daa9e3f793dedd3d8c3
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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