Diisopropylethylamine → tert-Butyl (2-(allyl(benzyl)amino)-2-oxoethyl)(benzyl)carbamate

HRID 2264834Notes

Reaction equation

HRID 2264834 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:51]1([CH2:57][NH:58][CH2:59][CH:60]=[CH2:61])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C=O)C.C(OCC)(=O)C>[O:12]=[C:10]([N:58]([CH2:57][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:59][CH:60]=[CH2:61])[CH2:9][N:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 521150N-AllylbenzylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 105158162-(Benzyl(tert-butoxycarbonyl)amino)acetic acid

Product 1

HCID 59596676tert-Butyl (2-(allyl(benzyl)amino)-2-oxoethyl)(benzyl)carbamateYield 95.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-{[(1,1-dimethylethyl)oxy]carbonyl}-N-(phenylmethyl)glycine (D88, 1.06 g, 4.0 mmol), DIPEA (1.38 ml, 8.0 mmol) and TBTU (1.61 g, 5.0 mmol) in dry DMF (8 ml) was stirred at room temperature for 30 min. Then N-(phenylmethyl)-2-propen-1-amine (D87, 647 mg, 4.4 mmol) was added and stirring was continued for another 2 h. After reaction was completed, ethyl acetate was added and the organic layer was washed with water and brine. The residue was purified via flash chromatography to give the title compound (1.50 g, 95%). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.4-7.2 (m, 10H), 5.8-5.5 (m, 1H), 5.2-5.0 (m, 2H), 4.7-4.3 (m, 4H), 4.1-3.7 (m, 4H), 1.5 (s, 9H); MS: (ES/+) m/z: 295 [M-BOC+], C24H30N2O3 requires 394.

Workup

  1. customAfter reaction
  2. washthe organic layer was washed with water and brine
  3. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-fd74f7aa3da5477b96ea6443a93a3ebe
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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