Diisopropylethylamine → 1,1-Dimethylethyl (2-{[(4-bromo-5-chloro-2-thienyl)carbonyl]amino}-3-phenylpropyl)carbamate

HRID 1845420Notes

Reaction equation

HRID 1845420 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][C:3]=1C.C(N(C(C)C)CC)(C)C.C1CN([P+]([Br:36])(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:44][CH:45]([CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[CH2:46][NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51]>C(Cl)Cl>[Br:36][C:3]1[CH:4]=[C:5]([C:7]([NH:44][CH:45]([CH2:55][C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH2:46][NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:51])[CH3:52])=[O:9])[S:6][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 126059575-Chloro-4-methylthiophene-2-carboxylic acidHCID 20159911tert-butyl N-(2-amino-3-phenylpropyl)carbamate

Product 1

HCID 578267421,1-Dimethylethyl (2-{[(4-bromo-5-chloro-2-thienyl)carbonyl]amino}-3-phenylpropyl)carbamateYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-4-methyl-2-thiophenecarboxylic acid (242 mg, 1.0 mmol) and diisopropylethyl amine (2.5 mL, 14.60 mmol) in DCM (50 mL) at 25° C. was added PyBrOP (2.5 g, 5.30 mmol) in one portion. After 30 min, 1,1-dimethylethyl (2-amino-3-phenylpropyl)carbamate (250 mg, 1.0 mmol) was added at one portion. After 2 h, the solution was concentrated and purified via column chromatography (silica, 10-40% EtOAc in Hexane) affording the title compound (460 mg, 97%) as a white solid: LC-MS (ES) m/z=474 (M+H)+.

Workup

  1. waitAfter 2 h
  2. concentrationthe solution was concentrated
  3. custompurified via column chromatography (silica, 10-40% EtOAc in Hexane)

Sources & evidence

ORD record
ord-2ea51f247b664a6d8397b47f47974c9a
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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