Cyclopropanesulfonyl chloride → (S)-2-[4-(4-Cyclopropanesulfonylamino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine1-carboxylic acid benzylester

HRID 737176Notes

Reaction equation

HRID 737176 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:31]1([S:34](Cl)(=[O:36])=[O:35])[CH2:33][CH2:32]1>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][S:34]([CH:31]3[CH2:33][CH2:32]3)(=[O:36])=[O:35])=[CH:27][CH:28]=2)[N:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2760919Cyclopropanesulfonyl chlorideHCID 86616427(S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester2×

Product 1

HCID 57849878(S)-2-[4-(4-Cyclopropanesulfonylamino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine1-carboxylic acid benzylester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of (S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (Compound 5050, Example 50, 0.06 g, 0.14 mmol) in DCM (2.0 mL) at 0° C. was added TEA (0.0.025 mL) followed by addition of cyclopropanesulfonyl chloride (0.016 mL). The reaction mixture was stirred at room temperature for 1 h then was concentrated in vacuo to give the crude product. Purification of the crude product by reverse phase HPLC furnished the desired product. 1HNMR (DMSO-d6) δ(ppm) 7.87-7.83 (m, 2H), 7.37-7.07 (m, 7H), 5.17-5.13 (m, 2H), 4.89-4.87 (m, 3H), 4.52-4.47 (m, 1H), 3.69-3.54 (m, 2H), 2.60-2.56 (m, 1H), 2.38-2.35 (m, 1H), 2.08-1.96 (m, 3 H), 1.07-0.95 (m, 4H); MS: 527.1 (M+H+).

Workup

  1. additionwas added TEA (0.0.025 mL)
  2. concentrationthen was concentrated in vacuo
  3. customto give the crude product
  4. customPurification of the crude product by reverse phase

Sources & evidence

ORD record
ord-ec32f106ec7e40c3826e25e934342329
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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