Aniline → HCID 86726294, compound

HRID 1422874Notes

Reaction equation

HRID 1422874 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CCOC(C)=O.CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:12])[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 11172571HCID 11172571, compound

Product 1

HCID 86726294HCID 86726294, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-2-tert-butoxycarbonylamino-hept-6-enoic acid (5.24 mmol), DIPEA (15.7 mmol) and aniline (5.76 mmol) was stirred at RT in DCM (70 ml) for 20 minutes before adding PyBOP (5.24 mmol) and anhydrous DMF (5 ml). The reaction mixture was stirred for 2 hours at RT. The solvent was removed under reduced pressure and the crude reaction mixture was diluted with AcOEt, washed with 5% Na2CO3, water and then with 5% aqueous citric acid and finally with brine. After removal of the solvent under reduced pressure and purification on silica gel (n-hexane/AcOEt: 9/1) the desired adduct was obtained.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude reaction mixture
  3. washwashed with 5% Na2CO3, water
  4. customAfter removal of the solvent
  5. customunder reduced pressure and purification on silica gel (n-hexane/AcOEt: 9/1) the desired adduct
  6. customwas obtained

Sources & evidence

ORD record
ord-a6f43cd133c74369aa29a7bfb23bd6bc
Source dataset
uspto-grants-2015_01
Patent number
US08927533B2

Reaction notes

Loading…