o-Toluenesulfonyl chloride → HCID 19705505, compound

HRID 727563Notes

Reaction equation

HRID 727563 reaction equation
[C:1]1(C)[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:12][CH2:13][CH2:14][CH:15]([C:23]1([CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]1=[O:36])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[CH:41](N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:41][C:5]1[CH:6]=[CH:1][C:2]([S:7]([NH:12][CH2:13][CH2:14][CH:15]([C:23]2([CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]2=[O:36])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:8])=[O:9])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8623o-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 19705515HCID 19705515, compound

Product 1

HCID 19705505HCID 19705505, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Toluenesulfonyl chloride (372 mg) is added to a solution of tert-butyl α-(2-aminoethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (EXAMPLE 73, step 1; 654 mg, 1.62 mmol), CH2Cl2 (10.0 mL), and diisopropylethylamine (0.34 mL) at 0° C. The solution is stirred at 0° C. for 1 hour and at room temperature for 16 hours. Basic workup (CH2Cl2, NaHCO3, MgSO4) and purification by flash chromatography gives 634 nag (70%) of the title compound as a white solid (mp 136°-138° C.):

Workup

  1. customBasic workup (CH2Cl2, NaHCO3, MgSO4) and purification by flash chromatography

Sources & evidence

ORD record
ord-b328905d2799435a8875dc178cf6f827
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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