Triethylamine → HCID 10477539, compound

HRID 2394478Notes

Reaction equation

HRID 2394478 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[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[N+:37]([O-:39])=[O:38])[C:31](Cl)=[O:32]>C(Cl)Cl>[F:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[N+:37]([O-:39])=[O:38])[C:31]([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:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 208636Di-tert-butyl glutamate hydrochlorideHCID 27746563-Fluoro-4-nitrobenzoyl chloride

Product 1

HCID 10477539HCID 10477539, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of di-tert butyl L-glutamate hydrochloride (20.0 g, 67.6 mol) in Et3N (19 ml, 136.0 mmol) was added dropwise a solution of 3-fluoro,4-nitro benzoyl chloride (13.8 g, 68.0 mmol) in CH2Cl2 (300 ml). Extractive workup gave an oil (13); yield (28.0 g, 97%); 1 H NMR (Me2SO-d6) δ1.40 (s, 9H, t-Bu), 1.42 (s, 9H, t-Bu), 1.99 (m, 2H, CH2CH2CO2 -t-Bu), 2.36 (t, 2H, J=7.45 Hz, CH2CH2CO2 -t-Bu), 4.35 (m, 1H, CH), 7.92 (dd, 1H, JH-6,H-5 =7.56 Hz, H-6), 8.01 (dd, 1H, JH-2,F =11.97 Hz, H-2), 8.29 (dd, 1H, JH-5,H-6 =7.83, JH-5,F =16.10 Hz, H-5), 8.97 (d, 1H, J=7.42 Hz, NH); 9F NMR (Me2SO-d6) δ-117.98 (dd, JF,H-2 =7.32, JF,H-5 =17.8 Hz); mass spectrum (CI) m/z 427 ([M+H+ ], 100); Anal: C20H27N2O7 F-0.25CH2Cl2 requires C-54.33, H-6.19, N-6.26, F-4.24, Cl-3.96, found C-54.22, H-6.38, N-6.05, F-4.34, Cl-4.15. (The presence of CH2 Cl2 noted in the elemental analysis was confirmed by NMR).

Sources & evidence

ORD record
ord-d60d0cb366474baf82e71471589a1416
Source dataset
uspto-grants-1998_09
Patent number
US05811454

Reaction notes

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