Ethyl Acetate → {4-[2-(3-Chlorophenyl)ethylcarbamoyl]thiazol-2-ylmethyl}carbamic acid tert-butyl ester

HRID 1009194Notes

Reaction equation

HRID 1009194 reaction equation
C([CH:8]([NH2:17])[C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)(OC(C)(C)C)=O.CN(C(ON1N=NC2[CH:29]=[CH:30][CH:31]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:42]CN(C(C)C)C(C)C.[Cl:51][C:52]1[CH:53]=[C:54]([CH2:58][CH2:59][NH2:60])[CH:55]=[CH:56][CH:57]=1.CC[O:63][C:64](C)=[O:65]>O.CN(C=O)C>[C:30]([O:65][C:64](=[O:63])[NH:17][CH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:16])[NH:60][CH2:59][CH2:58][C:54]2[CH:55]=[CH:56][CH:57]=[C:52]([Cl:51])[CH:53]=2)[N:13]=1)([CH3:29])([CH3:31])[CH3:42]

Participants

8

Reactant 5

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1393813-ChlorophenethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 571162792-(Boc-aminomethyl)thiazole-4-carboxylic acid

Product 1

HCID 67304673{4-[2-(3-Chlorophenyl)ethylcarbamoyl]thiazol-2-ylmethyl}carbamic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(Boc-aminomethyl)thiazole-4-carboxylic acid (0.5 g, 1.9 mmol) and HATU (0.81 g, 2.1 mmol) were weighed into a flask. DMF (7 mL) and DIEA (0.68 mL, 3.9 mmol) were added. The mixture was stirred for 10 minutes. 2-(3-Chlorophenyl)ethylamine (0.3 g, 1.9 mmol) was added and reaction mixture was stirred for 12 hours. The mixture was diluted EtOAc and water. The layers were separated and the aqueous layer was extracted with 3×EtOAc. The combined organic layers were washed with 5% aqueous lithium chloride and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The material was purified by filtration through a plug of silica gel with 1:1 EtOAc:hexane to afford the title compound (0.73 g, 95%): 1H NMR (400 MHz, d6-DMSO): 8.42 (t, 1H), 8.10 (s, 1H), 7.85 (t, 1H), 7.27 (m, 3H), 7.16 (m, 1H), 4.38 (d, 2H), 3.46 (q, 2H), 2.82 (t, 2H), 1.39 (s, 9H); MS (ESI-LCMS) for C14H14ClN3O3S: 340 (MH-tBu+).

Workup

  1. customreaction mixture
  2. stirringwas stirred for 12 hours
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with 3×EtOAc
  5. washThe combined organic layers were washed with 5% aqueous lithium chloride and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. filtrationThe material was purified by filtration through a plug of silica gel with 1:1 EtOAc

Sources & evidence

ORD record
ord-9979a898f8b24623aef3fd911f95cf19
Source dataset
uspto-grants-2011_07
Patent number
US07973061B2

Reaction notes

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