Diisopropylethylamine → 1,1-Dimethylethyl (2-{[(5-bromo-2-thienyl)carbonyl]amino}-2-phenylethyl)carbamate

HRID 1845370Notes

Reaction equation

HRID 1845370 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:43][CH:44]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:45][NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50]>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([C:7]([NH:43][CH:44]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:45][NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:50])[CH3:51])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3491155-Bromothiophene-2-carboxylic acidHCID 2733179PyBroPHCID 2771847tert-butyl N-(2-amino-2-phenylethyl)carbamate

Product 1

HCID 578266691,1-Dimethylethyl (2-{[(5-bromo-2-thienyl)carbonyl]amino}-2-phenylethyl)carbamateYield 299.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-thiophenecarboxylic acid (3.2 g, 15.2 mmol), PyBrOP (8.5 g, 18.2 mmol) and diisopropylethyl amine (10.6 mL, 60.9 mmol) in DCM (76 mL) at 25° C. was added 1,1-dimethylethyl (2-amino-2-phenylethyl)carbamate (3.6 g, 3.14 mmol) [prepared in Preparation 1]. After 16 h, the solution was partitioned between H2O and washed with DCM. The combined organic fraction were dried (Na2SO4), concentrated and purified via column chromatography (silica, 1% MeOH in DCM) affording the title compound (4 g, 62%) as a white solid: LC-MS (ES) m/z=426 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O
  2. washwashed with DCM
  3. dry with materialThe combined organic fraction were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography (silica, 1% MeOH in DCM)

Sources & evidence

ORD record
ord-531e7156d92c4e7ab5bc58c2b91e4d07
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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