m-Toluidine → HCID 68730771, compound

HRID 1523233Notes

Reaction equation

HRID 1523233 reaction equation
[CH3:1][C:2]([CH3:19])([S@@:4]([NH:6][C@:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH2:8][C:9]([OH:11])=O)=[O:5])[CH3:3].[C:20]1([CH3:27])[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][C:2]([CH3:1])([S@@:4]([NH:6][C@:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH2:8][C:9]([NH:26][C:22]1[CH:21]=[C:20]([CH3:27])[CH:25]=[CH:24][CH:23]=1)=[O:11])=[O:5])[CH3:3]

Participants

6

Reactant 3

HCID 7934m-ToluidineHCID 10868DicyclohexylcarbodiimideHCID 68731246HCID 68731246, compound

Product 1

HCID 68730771HCID 68730771, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-((S)-1,1-dimethylethylsulfinamido)-3-phenylbutanoic acid (266 mg, 0.94 mmol) in CH2Cl2 (5 mL) was added m-tolylamine (111 mg, 1.03 mmol), DCC (212 mg, 1.03 mmol) and DMAP (11.5 mg, 0.094 mmol) at 0° C. Then the reaction mixture was stirred at room temperature overnight. The residue was purified by preparative TLC to give (R)-3-((S)-1,1-dimethylethylsulfinamido)-3-phenyl-N-m-tolylbutanamide (25 mg, 7%). 1H NMR (CDCl3): 1.10-1.20 (m, 12H), 1.51-1.65 (m, 11H), 3.10-3.30 (m, 2H), 4.25 (s, 1H), 6.80-6.90 (m, 1H), 7.06-7.15 (m, 1H), 7.28-7.48 (m, 5H), 7.50-7.60 (m, 2H), 8.95 (s, 1H).

Workup

  1. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-07a7ca14f71f49e2aa86015c9b692f83
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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