Diisopropylethylamine → 3-(aminomethyl)benzoic acid

HRID 376788Notes

Reaction equation

HRID 376788 reaction equation
N(C(OC(C)(C)C)=O)[C@@H:2]([C:14]([OH:16])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6]NC(C(F)(F)F)=O.[CH3:24][N:25](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:48]CN(C(C)C)C(C)C>C(Cl)Cl.C(OCC)(=O)C>[NH2:25][CH2:24][C:6]1[CH:48]=[C:2]([CH:3]=[CH:4][CH:5]=1)[C:14]([OH:16])=[O:15]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 6993446(R)-2-((tert-Butoxycarbonyl)amino)-6-(2,2,2-trifluoroacetamido)hexanoic acid

Product 1

HCID 5060733-(aminomethyl)benzoic acidYield 457.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

NMeArg(Tos)-Gly-OBzl (14.40 g, 29.4 mmol), Boc-D-Lys(Tfa) (10.00 g, 29.4 mmol), and HBTU (11.37 g, 62.0 mmol) were dissolved in methylene chloride (40 ml). After cooling to 0° C., DIEA (10.44 g, 62.0 mmol) was added and the reaction was allowed to proceed 20 minutes at 0° C. and 2 days at room temperature. The reaction mixture was diluted with ethyl acetate (800 ml), extracted with 200 ml portions of 0.2 N HCl (1×), sat. NaHCO3 (1×), and saturated NaCl (2×), dried (MgSO4), and evaporated under reduced pressure to a yellow solid. Purification by flash chromatography (silica gel; 5:1 EtOAc:acetonitrile) gave the title compound as a colorless solid (20.34 g, 85%). MP 78-85° C.; DCI-MS: [M+NH4 ]=831.

Workup

  1. extractionextracted with 200 ml portions of 0.2 N HCl (1×), sat. NaHCO3 (1×), and saturated NaCl (2×)
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure to a yellow solid
  4. customPurification by flash chromatography (silica gel; 5:1 EtOAc:acetonitrile)

Sources & evidence

ORD record
ord-b2fce1e53e174348a3a16bacab67a43f
Source dataset
uspto-grants-2000_02
Patent number
US06022523

Reaction notes

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