Diisopropylamine → HCID 21070243, compound

HRID 1371539Notes

Reaction equation

HRID 1371539 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:22]([NH:25][CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=1)[C:10]([N:25]([CH:26]([CH3:28])[CH3:27])[CH:22]([CH3:24])[CH3:23])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 8471TriethylamineHCID 2733179PyBroPHCID 43933462-Tert-butoxycarbonylamino-3-(4-cyano-phenyl)-propionic acid

Product 1

HCID 21070243HCID 21070243, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1 g of 2-(tert-butoxycarbonylamino)-3-(4-cyanophenyl)propionic acid and 0.540 g of diisopropylamine in 10 ml of DCM is cooled to 0° C., 0.960 ml of triethylamine is added, followed by addition of 1.76 g of bromotripyrrolidinophosphonium hexafluorophosphate, and the mixture is stirred for 2 hours and allowed to warm to RT. The reaction mixture is concentrated under vacuum, the residue is extracted with EtOAc, the organic phase is washed with water, with 5% KHSO4 solution, with water, with saturated NaHCO3 solution and with saturated NaCl solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with a heptane/EtOAc mixture (80/20; v/v). 0.4 g of the expected product is obtained; m.p.=172° C.

Workup

  1. temperatureto warm to RT
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. extractionthe residue is extracted with EtOAc
  4. washthe organic phase is washed with water, with 5% KHSO4 solution, with water, with saturated NaHCO3 solution and with saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a heptane/EtOAc mixture (80/20; v/v)

Sources & evidence

ORD record
ord-5980ba7a206745e889a10806ee087347
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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