HCID 22726892, compound → HCID 22726793, compound

HRID 2085968Notes

Reaction equation

HRID 2085968 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:6]=1.[CH3:19][C:20]([CH3:23])([O-:22])[CH3:21].[Na+]>C(O)(C)C.C(O)(C)(C)C>[C:20]([O:22][C:12]([NH:11][CH2:10][CH2:9][S:8][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:6]=1)=[O:13])([CH3:23])([CH3:21])[CH3:19]

Participants

5

Reactant 2

HCID 22726892HCID 22726892, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 22726793HCID 22726793, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromo-4-[(2-tert-butoxycarbonylaminoethyl)thiomethyl]-1,3-thiazole (421 mg, 1.2 mmol) and 2-(tert-butoxycarbonylamino)ethylthiol (234 mg, 1.3 mmol) in isopropyl alcohol (5 mL) was added 1.0 M sodium t-butoxide in t-butanol (1.2 mL) and stirred at 80° C. for 1 h. After cooling, the mixture was concentrated and partitioned between ethyl acetate and water. The ethyl acetate extract was concentrated. The residue was chromatographed on silica gel (1% methanol/dichloromethane), affording 364 mg of the title compound. 1H NMR (CDCl3) δ 1.63 (18H), 2.78 (t, 2H), 3.42 (m, 4H), 3.61 (t, 2H), 3.90 (s, 2H), 5.18 (br s, 1H), 7.13 (1H).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. extractionThe ethyl acetate extract
  5. concentrationwas concentrated
  6. customThe residue was chromatographed on silica gel (1% methanol/dichloromethane)

Sources & evidence

ORD record
ord-3caa5cf30e2a4f2b9f87f10710472165
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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