Benzhydrylpiperazine → HCID 131724627, compound

HRID 393982Notes

Reaction equation

HRID 393982 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([N:14]2[CH2:18][C@@H:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][C@H:15]2[C:26]([OH:28])=O)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:29]1([CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([N:51](CC)C(C)C)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH:35]([N:36]1[CH2:37][CH2:38][N:39]([NH:51][C:26]([C@@H:15]2[CH2:16][C@H:17]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][N:14]2[S:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)(=[O:13])=[O:12])=[O:28])[CH2:40][CH2:41]1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 70048BenzhydrylpiperazineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 23531923HCID 23531923, compound

Product 1

HCID 131724627HCID 131724627, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3,4-Dimethoxybenzenesulfonyl)-[(2S,4S)-4-phenoxy-2-pyrrolidinecarboxylic acid] (10) (0.64 g; 1.57 mmol) is dissolved in methylene chloride (15 mL) at ambient temperature. 1-(Diphenylmethyl)piperazine (0.48 g; 1.89 mmol), N,N-diisopropylethylamine (0.45 g; 3.46 mmol) and PyBOP (0.98 g; 1.89 mmol) are added sequentially. The reaction is stirred for 16 hours at room temperature, then concentrated under reduced pressure. The residue is purified via silica gel chromatography (40%→50% ethyl acetate in hexanes) affording the desired product as a solid foam. CIMS: MH+ 642

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified via silica gel chromatography (40%→50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f7614024312b41cd8d1a84945bfcf35b
Source dataset
uspto-grants-2004_10
Patent number
US06809093B2

Reaction notes

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