Triethylamine → di-tert-butyl (2,3,4,5-tetrafluorobenzoyl)-L-glutamate

HRID 23610

Reaction equation

HRID 23610 reaction equation
Cl.[NH2:2][C@H:3]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CCN(CC)CC.[F:27][C:28]1[C:36]([F:37])=[C:35]([F:38])[C:34]([F:39])=[CH:33][C:29]=1[C:30](Cl)=[O:31]>C(Cl)Cl>[F:27][C:28]1[C:36]([F:37])=[C:35]([F:38])[C:34]([F:39])=[CH:33][C:29]=1[C:30]([NH:2][C@H:3]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 208636Di-tert-butyl glutamate hydrochlorideHCID 27336892,3,4,5-Tetrafluorobenzoyl chloride

Product 1

HCID 11270493di-tert-butyl (2,3,4,5-tetrafluorobenzoyl)-L-glutamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of di-tert-butyl L-glutamate hydrochloride (6.6 g, 22.4 mmol) and Et3N (6.9 ml, 50 mmol) in dry CH2Cl2 (70 ml) was added, over a period of 1.5 hr, 2,3,4,5-tetrafluorobenzoyl chloride (5.0 g, 23.5 mmol) in dry CH2Cl2 (20 ml) and thirty minutes later the solution was allowed to warm to room temperature. Sixteen hours later the solution was washed with H2O, dried (MgSO4) and evaporated to dryness. 1H NMR δ 1.40+1.42 (2s, 18H, t-butyl), 1.85+1.95 (2m, 2H, CH2CH), 2.34 (t, 2H, CH2CO, J=7.5 Hz), 4.3 (m, 1H, CH), 7.57 (m, 1H, H6), 8.80 (d, 1H, NH, J=7.5 Hz); 19F NMR δ −138.6+139.0 (2m, 2F, F2+5), −152.4 (m, 1H, F4), −154.9 (t, 1F, F3, J=20 Hz).

Workup

  1. washSixteen hours later the solution was washed with H2O
  2. dry with materialdried (MgSO4)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-b2e52de445c646f1a9a2145db1d992a4
Source dataset
uspto-grants-2005_02
Patent number
US06852755B1

Linked notes

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