Diisopropylethylamine → HCID 131725142, compound

HRID 496232Notes

Reaction equation

HRID 496232 reaction equation
Cl.[CH3:2][C@@:3]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4]1.[Cl:12][C:13]1[CH:14]=[C:15]([S:20](Cl)(=[O:22])=[O:21])[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(N(C(C)C)CC)(C)C>C1COCC1.C(Cl)Cl>[Cl:19][C:17]1[CH:16]=[C:15]([S:20]([N:4]2[CH2:5][CH2:6][CH2:7][C@@:3]2([CH3:2])[C:8]([O:10][CH3:11])=[O:9])(=[O:21])=[O:22])[CH:14]=[C:13]([Cl:12])[CH:18]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 575164552-Methyl-L-proline Methyl ester hydrochloride

Product 1

HCID 131725142HCID 131725142, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-methyl-(L)-proline, methyl ester hydrochloride (95 gm, 52.9 mmol) was dissolved in a mixture (1:1) of dry THF and CH2Cl2 (250 mL). A solution of 3,5-dichlorobenzenesulfonyl chloride (13.0 gm, 52.9 mmol) in dry CH2Cl2 (20 mL) was added. The reaction was cooled in an ice bath and diisopropylethylamine (20.5 gm, 158.6 mmol) was added. The ice bath was removed and the reaction mixture was stirred overnight at rt. The reaction was concentrated and dried to a tan solid (18.68 gm). This solid was purified on a Biotage 40M chromatography system eluted with 10% EtOAc in hexanes to yield N-(3,5-dichlorobenzenesulfonyl)-2-methyl-(L)-proline, methyl ester as a pure white solid (16.8 gm, 85% yield).

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customThe ice bath was removed
  3. concentrationThe reaction was concentrated
  4. dry with materialdried to a tan solid (18.68 gm)
  5. customThis solid was purified on a Biotage 40M chromatography system
  6. washeluted with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-f4f7f383179b47dfb2abcefd7681053e
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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