Triethylamine → HCID 54264483, compound

HRID 1768913Notes

Reaction equation

HRID 1768913 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13](Cl)(=[O:15])=[O:14].Cl.[C:19]([O:23][C:24](=[O:34])[C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30](=[O:33])[CH2:31][NH2:32])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[C:19]([O:23][C:24](=[O:34])[C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30](=[O:33])[CH2:31][NH:32][S:13]([C:8]1[C:9]2[C:4](=[C:3]([N:2]([CH3:17])[CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:15])=[O:14])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 57383535tert-Butyl glycyl-L-prolinate--hydrogen chloride (1/1)

Product 1

HCID 54264483HCID 54264483, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Dimethylamino-l-naphthalenesulfonyl chloride (5.10 g, 18.9 mmol) was added in portions to a well-stirred solution of glycyl-L-proline tert-butyl ester hydrochloride (5.00 g, 18.9 mmol) and triethylamine (5.20 mL, 37.8 mmol) in dry tetrahydrofuran (175 mL). The mixture was stirred at room temperature for 4 hours before it was diluted with ethyl acetate and washed successively with saturated sodium bicarbonate solution and brine. Following drying and solvent evaporation, the residue was chromatographed on silica gel (gradient elution with first 40% ethyl acetate in hexanes followed by 50% ethyl acetate in hexanes) and furnished 7.62 g (87%) of the title compound as a fluorescent green foam, m.p. 60°-67° C.; 1H NMR (CDCl3) δ 8.51 (dd, J=8.5, 3.3 Hz, 1H), 8.30 (d, J=8.7 Hz, 1H), 8.21-8.16 (m, 1H), 7.58-7.43 (m, 2H), 7.15 (d, J=7.4 Hz, 1H), 5.85-5.79 (m, 1H), 4.27-4.23 (m, 1H), 3.76-3.62 (m, 2H), 3.48-3.21 (m, 2H), 2.84 (s, 6H), 2.10-1.75 (m, 4H), 1.33 and 1.32 (2s, 9H); 13C NMR (CDCl3) ppm 170.84, 170.45, 165.84, 165.46, 152.04, 134.31, 134.16, 130.79, 130.16, 130.12, 129.87, 129.52, 129.47, 128.77, 123.23, 123.17, 119.22, 119.13, 115.59, 83.00, 81.82, 59.99, 59.38, 46.97, 45.98, 45.64, 44.69, 44.58, 31.41, 29.13, 28.05, 27.96, 24.49, 23.80, 22.36; IR (KBr, cm-1) 3266, 2978, 2942, 2876, 2834, 1736, 1658, 1456, 1440, 1370, 1330, 1148, 792, 626, 574; MS m/z (MH+) calcd 461.1984, obsd 461.1982.

Workup

  1. washwashed successively with saturated sodium bicarbonate solution and brine
  2. customFollowing drying
  3. customsolvent evaporation
  4. customthe residue was chromatographed on silica gel (gradient elution with first 40% ethyl acetate in hexanes followed by 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0744f8bbf9a747d19cc35affc60c72c1
Source dataset
uspto-grants-1995_01
Patent number
US05380713

Reaction notes

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