Water → HCID 67077419, compound

HRID 2233152Notes

Reaction equation

HRID 2233152 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:13]([S:14](Cl)(=[O:16])=[O:15])=[C:12]([Cl:18])[CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[C:26]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].O>C1COCC1>[C:29]([O:28][C:26]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH:34]1[S:14]([C:13]1[C:7]2[O:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:9][C:8]=2[CH:10]=[CH:11][C:12]=1[Cl:18])(=[O:16])=[O:15])=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 234477912-Tert-butyl-6-chlorobenzoxazole-7-sulfonyl chloride

Product 1

HCID 67077419HCID 67077419, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl chloride (10.75 g, 34.9 mmol) in 100 mL of THF was cooled to 0° C., Et3N (3.47 mL, 24.9 mmol) and then Boc-piperazine (5.0 g, 26.8 mmol) were added. The resulting mixture was stirred for 20 h, warming to room temperature. The mixture was poured into water, extracted with EtOAc and washed with another portion of water; organic layers were dried and concentrated. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (30/70, v/v), yielded 11.12 g (91%) desired product 1c. LC-MS (m/z) 458.2 (M+H).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with another portion of water
  3. customorganic layers were dried
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel
  6. washeluting with ethyl acetate/hexane (30/70

Sources & evidence

ORD record
ord-df0a367d560d4901a7566408caf8327e
Source dataset
uspto-grants-2010_05
Patent number
US07709485B2

Reaction notes

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