2,4-Dichlorobenzoyl chloride → 2-[(3-Bromo-thiophen-2-ylmethyl)-(2,4-dichloro-benzoyl)-amino]-3-phenyl-propionic acid tert-butyl ester

HRID 2179923Notes

Reaction equation

HRID 2179923 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH:7]([NH:15][CH2:16][C:17]1[S:18][CH:19]=[CH:20][C:21]=1[Br:22])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>ClCCl.C(N(CC)C(C)C)(C)C>[C:1]([O:5][C:6](=[O:23])[CH:7]([N:15]([CH2:16][C:17]1[S:18][CH:19]=[CH:20][C:21]=1[Br:22])[C:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:32]([Cl:34])=[CH:33][C:25]=1[Cl:24])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 207793132-[(3-Bromo-thiophen-2-ylmethyl)-amino]-3-phenyl-propionic acid tert-butyl ester

Product 1

HCID 207793122-[(3-Bromo-thiophen-2-ylmethyl)-(2,4-dichloro-benzoyl)-amino]-3-phenyl-propionic acid tert-butyl esterYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a stirred solution of 2-[(3-Bromo-thiophen-2-ylmethyl)-amino]-3-phenyl-propionic acid tert-butyl ester (91.6 mg, 0.231 mmol) in dichloromethane (3.3 ml) and N,N-diisopropylethylamine (44 μl) was added a solution of 2,4-Dichloro-benzoyl chloride (34 μl, 0.243 mmol) in dichloromethane (1.3 ml). The reaction mixture was stirred at room temperature under nitrogen overnight. Then, the mixture was extracted with sodium bicarbonate/dichloromethane. The extract was dried (sodium sulfate) and evaporated under reduced pressure to yield 2-[(3-Bromo-thiophen-2-ylmethyl)-(2,4-dichloro-benzoyl)-amino]-3-phenyl-propionic acid tert-butyl ester with 92% yield. 1H NMR(Varian 400 MHz, CDCl3) δ(ppm) presence of rotomers 8.08 (d, 0.5H, J=8.7 Hz, ArH), 7.56 (d, 0.5H, J=2.0 Hz, ArH), 7.40 (m, 2H, ArH), 7.23 (m, 2.5H, ArH), 6.99 (d, 0.5H, J=5.4 Hz, ArH), 6.92 (m, 2H, ArH), 6.83 (d, 0.5H, J=5.0 Hz, ArH), 6.54 (d, 1H, J=7.1 Hz, ArH), 5.78 (d, 0.5H, J=8.0 Hz, ArH), 5.20 (m, 1H, NCH2), 4.85 (m, 1H, NCH2), 4.16 (m, 1H, CHCH2), 3.10 (m, 2H, CHCH2), 1.47 (s, 9H, tBu).

Workup

  1. extractionThen, the mixture was extracted with sodium bicarbonate/dichloromethane
  2. dry with materialThe extract was dried (sodium sulfate)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-77c092fff2334251925a7a89c188d9c5
Source dataset
uspto-grants-2005_05
Patent number
US06887877B2

Reaction notes

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