(2-chloro-1,3-thiazol-5-yl)methyl N-phenylcarbamate → [2-(4-{[(2-t-Butoxycarbonylaminophenyl)amino]carbonyl}phenyl)-1,3-thiazol-5-yl]methyl phenylcarbamate

HRID 888044Notes

Reaction equation

HRID 888044 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33]1([NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]2[S:47][C:46](Cl)=[N:45][CH:44]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(OCC)(=O)C.O>[C:33]1([NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]2[S:47][C:46]([C:20]3[CH:19]=[CH:18][C:17]([C:16]([NH:15][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:32])=[CH:22][CH:21]=3)=[N:45][CH:44]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 1479740(2-chloro-1,3-thiazol-5-yl)methyl N-phenylcarbamateHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 1

HCID 68407987[2-(4-{[(2-t-Butoxycarbonylaminophenyl)amino]carbonyl}phenyl)-1,3-thiazol-5-yl]methyl phenylcarbamate

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

Using an analogous procedure to that described in Method 4, N-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Method 13, 219 mg, 0.5 mmol) was reacted with (2-chloro-1,3-thiazol-5-yl)methyl N-phenylcarbamate (136 mg, 0.5 mmol). The crude residue stirred in ethyl acetate/water for 16 hours before being filtered, and the aqueous removed using a Varian Chem Elut Column (CE1010). The resulting solution was concentrated and purified by flash chromatography on silica, eluting with methanol/dichloromethane (0-30%) to give the title compound; Mass Spectrum: M+H+-Boc 489.

Workup

  1. filtrationbefore being filtered
  2. customthe aqueous removed
  3. concentrationThe resulting solution was concentrated
  4. custompurified by flash chromatography on silica
  5. washeluting with methanol/dichloromethane (0-30%)

Sources & evidence

ORD record
ord-80c973e52b71404fa1e4f62395de1e78
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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