4-Methylmorpholine → N-[2,3-Bis(4-chlorophenyl)-1-methylpropyl]-2-(4-chlorophenylamino)-2-methylpropanamide

HRID 488628Notes

Reaction equation

HRID 488628 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:10]([NH2:12])[CH3:11])=[CH:5][CH:4]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([CH3:34])([CH3:33])[C:30](O)=[O:31])=[CH:24][CH:23]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.[PH4+]>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH:10]([NH:12][C:30](=[O:31])[C:29]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=2)([CH3:34])[CH3:33])[CH3:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2757757Alanine, N-(4-chlorophenyl)-2-methyl-HCID 21584439Phosphonium hexafluorophosphateHCID 222704272,3-Bis(4-chlorophenyl)-1-methylpropylamine hydrochloride

Product 1

HCID 22270589N-[2,3-Bis(4-chlorophenyl)-1-methylpropyl]-2-(4-chlorophenylamino)-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-amino-3,4-bis(4-chlorophenyl)butane hydrochloride salt (Diastereomer α, Section I, Reference Example 1, 0.31 g, 0.94 mmol) and 2-(4-chlorophenylamino)-2-methylpropionic acid (0.20 g, 0.94 mmol) in 5 mL CH2Cl2 was added N-methylmorpholine (0.41 mL, 3.5 mmol) and tris(pyrrolindinyl) phosphonium hexafluorophosphate (0.73 g, 1.4 mmol). After stirring at RT overnight, the reaction mixture was loaded onto a silica gel column eluted with 30% EtOAc in hexane to give the title compound. 1H NMR (400 MHz, CD3OD): δ 7.18 (d, 2H), 7.04 (d, 2H), 7.02 (d, 2H), 6.97 (d, 2H), 6.70 (d, 2H), 6.56 (d, 2H), 4.20 (m, 1H), 3.02 (dd, 1H), 2.78 (ddd, 1H), 2.64 (dd, 1H), 1.52 (s, 3H), 1.45 (s, 3H), 0.82 (d, 3H). LC-MS: m/e 489 (M+H)+ (4.3 min).

Workup

  1. washeluted with 30% EtOAc in hexane

Sources & evidence

ORD record
ord-7ca1b7643b9749c4b5eaae482b25a104
Source dataset
uspto-grants-2005_12
Patent number
US06972295B2

Reaction notes

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