Water → 3,5-dimethyl-4-([1,4]oxazepane-4-sulfonyl)-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2375805Notes

Reaction equation

HRID 2375805 reaction equation
Cl.[O:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH2:18]([O:20][C:21]([C:23]1[NH:24][C:25]([CH3:33])=[C:26]([S:29](Cl)(=[O:31])=[O:30])[C:27]=1[CH3:28])=[O:22])[CH3:19].O>C(Cl)Cl>[CH2:18]([O:20][C:21]([C:23]1[NH:24][C:25]([CH3:33])=[C:26]([S:29]([N:5]2[CH2:6][CH2:7][CH2:8][O:2][CH2:3][CH2:4]2)(=[O:30])=[O:31])[C:27]=1[CH3:28])=[O:22])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2776544ethyl 4-(chlorosulfonyl)-3,5-dimethyl-1H-pyrrole-2-carboxylateHCID 230902141,4-Oxazepane hydrochloride

Product 1

HCID 692881593,5-dimethyl-4-([1,4]oxazepane-4-sulfonyl)-1H-pyrrole-2-carboxylic acid ethyl esterYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [1,4]oxazepane hydrochloride (400 mg) in DCM (45 mL) was added DIEA (2.70 mL) followed by 4-chlorosulfonyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.05 g). The mixture was stirred for 1 h at RT after which water was added and the resulting two phases were separated. The organic phase was washed two times with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated to give crude) 3,5-dimethyl-4-([1,4]oxazepane-4-sulfonyl)-1H-pyrrole-2-carboxylic acid ethyl ester (970 mg) which was used directly in the following step.

Workup

  1. additionwas added
  2. customthe resulting two phases were separated
  3. washThe organic phase was washed two times with saturated aqueous NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e88dcafadfa04c56af0a42dc2674c4ef
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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