2-(Tributylstannyl)-1,3-thiazole → tert-butyl (1S,2S,4S)-4-amino-1-benzyl-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[4-(1,3-thiazol-2-yl)phenyl]pentylcarbamate

HRID 1174360Notes

Reaction equation

HRID 1174360 reaction equation
[CH2:1]([C@H:8]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[C@@H:9]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:10][C@@H:11]([NH:20]C(OCC1C=CC=CC=1)=O)[CH2:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:52]1[S:53][CH:54]=[CH:55][N:56]=1)CCC>CN(C)C=O.C(Cl)(Cl)Cl.[Ag-]=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:20][C@@H:11]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:52]2[S:53][CH:54]=[CH:55][N:56]=2)=[CH:17][CH:18]=1)[CH2:10][C@H:9]([O:31][Si:32]([C:35]([CH3:37])([CH3:38])[CH3:36])([CH3:34])[CH3:33])[C@@H:8]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:43])([CH3:44])[CH3:45])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 86726209tert-butyl (1S,2S,4S)-1-benzyl-4-{[benzyloxycarbonyl]amino}-5-(4-bromophenyl)-2-{[tert-butyl(dimethyl)silyl]oxy}pentylcarbamate

Product 1

HCID 86726241tert-butyl (1S,2S,4S)-4-amino-1-benzyl-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[4-(1,3-thiazol-2-yl)phenyl]pentylcarbamateYield 130.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 178418778HCID 178418778, compoundCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution containing the product from Example 92D (0.050 g, 0.070 mmol) in N,N-dimethylformamide (1.8 mL) were added silver(I) oxide (0.016 g, 0.070 mmol), tetrakis(triphenylphosphine)palladium (0.004 g, 0.003 mmol), and 2-tributylstannylthiazole (0.126 g, 0.337 mmol), and the mixture was irradiated at 60 W in a microwave (internal temperature reached 100° C.) for 2 minutes. The mixture was then irradiated at 200 W in a microwave (internal temperature reached 100° C.) for 4 minutes The reaction was cooled, diluted with chloroform and washed with dilute NaHCO3, and brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 30% methanol in chloroform containing 0.2% ammonium hydroxide to give the title compound (0.053 g).

Workup

  1. customthe mixture was irradiated at 60 W in a microwave (internal temperature reached 100° C.) for 2 minutes
  2. customThe mixture was then irradiated at 200 W in a microwave (internal temperature reached 100° C.) for 4 minutes The reaction
  3. temperaturewas cooled
  4. washwashed with dilute NaHCO3, and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with 30% methanol in chloroform containing 0.2% ammonium hydroxide

Sources & evidence

ORD record
ord-0f6272844de2443595070a86730e2e17
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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