Hydrochloric Acid → Tert-butyl 2-({[2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl]sulfanyl}carbonyl)hydrazinecarboxylate

HRID 1892540Notes

Reaction equation

HRID 1892540 reaction equation
[SH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1.[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22].[C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:36])[NH:34][NH2:35].Cl>O1CCCC1.C(OCC)(=O)C.O>[C:18]([NH:17][C:14]1[S:15][CH:16]=[C:12]([CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][S:1][C:21]([NH:35][NH:34][C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:22])=[CH:5][CH:6]=2)[N:13]=1)(=[O:20])[CH3:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazateHCID 86650044N-(4-{2-[4-(2-sulfanylethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

Product 1

HCID 86650045Tert-butyl 2-({[2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl]sulfanyl}carbonyl)hydrazinecarboxylateYield 84.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-{2-[4-(2-sulfanylethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (368.0 mg, 1.201 mmol) in anhydrous tetrahydrofuran (30 ml) was added 1,1′-carbonyldiimidazole (291.4 mg, 1.797 mmol), and the mixture was stirred at room temperature for 1 hr. tert-Butyl carbazate (477.9 mg, 3.616 mmol), anhydrous tetrahydrofuran (2 ml) was added, and the mixture was stirred at room temperature for 19 hr. Water (20 ml), 1M hydrochloric acid (10 ml) and ethyl acetate (30 ml) were added, and the mixture was stirred, stood still and partitioned. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 30 g, ethyl acetate:hexane=1:1) to give tert-butyl 2-({[2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl]sulfanyl}carbonyl)hydrazinecarboxylate (469.9 mg, 1.011 mmol, yield 84.2%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 19 hr
  2. stirringthe mixture was stirred
  3. custompartitioned
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 30 g, ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-6a63d2ca773f43dabea3e2467e253827
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

Loading…