tert-Butanol → 7-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-azepan-2-one

HRID 660554Notes

Reaction equation

HRID 660554 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].C(O)(C)(C)C.COC(=O)[CH2:16][NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27](=[O:32])[NH:26]2)=[CH:20][C:19]=1[O:33]CC1C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[OH:33][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][C:18]=1[N:17]1[CH2:16][C:6](=[O:7])[NH:5][S:2]1(=[O:4])=[O:3])[CH2:24][CH:25]1[NH:26][C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 68838479[2-Benzyloxy-4-(7-oxo-azepan-2-ylmethyl)-phenylamino]-acetic Acid Methyl Ester

Product 1

HCID 426296607-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-azepan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cooled solution of chlorosulfonyl isocyanate (315 mg, 2.22 mmol) in CH2Cl2 (8 mL) is added dropwise a solution of t-butanol (165 mg, 2.22 mmol) in CH2Cl2 (1 mL). The solution is stirred at RT for 45 min and re-cooled, then a solution of [2-benzyloxy-4-(7-oxo-azepan-2-ylmethyl)-phenylamino]-acetic acid methyl ester (600 mg, 1.48 mmol) and triethylamine (252 mg, 2.52 mmol) in CH2Cl2 (2 mL) is added dropwise. The mixture is stirred at RT for 3 h then washed with water. The organic phase is dried over Na2SO4 and the solvent is removed under reduced pressure. The residual oil is purified by flash chromatography using EtOAc/CH2Cl2 (1:1) as eluent to give the title compound.

Workup

  1. temperaturere-cooled
  2. stirringThe mixture is stirred at RT for 3 h
  3. washthen washed with water
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customthe solvent is removed under reduced pressure
  6. customThe residual oil is purified by flash chromatography

Sources & evidence

ORD record
ord-e01f17050e5e4ccc8424eb8489876997
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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