Benzenesulfonyl chloride → HCID 12069136, compound

HRID 1356206Notes

Reaction equation

HRID 1356206 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([CH2:10][C@H:11]([NH2:24])[C:12](=[O:23])[NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:5]=1[O:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].[C:32]1([S:38](Cl)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([CH2:10][C@H:11]([NH:24][S:38]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:40])=[O:39])[C:12](=[O:23])[NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:5]=1[O:25][CH2:26][C:27]([O:29][CH3:30])=[O:28]

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 12069135HCID 12069135, compound

Product 1

HCID 12069136HCID 12069136, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

5-[(2S)-2-Amino-2-(4-methoxy-benzylcarbamoyl)-ethyl]-2-methoxycarbonylmethoxy-benzoic acid methyl ester of Step G (40 mg, 0.072 mmol) is stirred in pyridine (0.5 mL) at 0° C. under N2. Benzenesulfonyl chloride (20 mg, 0.11 mmol) is added and the reaction is stirred overnight at RT. The mixture is then diluted with CH2Cl2 (20 mL), washed with 2N HCl (2×20 mL) and then with saturated NaHCO3 (2×20 mL). The organics are dried over MgSO4, filtered, concentrated and purified by flash column chromatography to provide 5-[(2S)-2-benzenesulfonylamino-2-(4-methoxy-benzylcarbamoyl)-ethyl]-2-methoxycarbonylmethoxy-benzoic acid methyl ester.

Workup

  1. washwashed with 2N HCl (2×20 mL)
  2. dry with materialThe organics are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-7663822e186946278891f037c106bdca
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

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