Chlorosuccinimide → HCID 58746513, compound

HRID 724612Notes

Reaction equation

HRID 724612 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[CH:4][CH:3]=1.[Cl:28]N1C(=O)CCC1=O>CN(C)C=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])=[CH:4][C:3]=1[Cl:28]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 70116510HCID 70116510, compound

Product 1

HCID 58746513HCID 58746513, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl (2S)-3-(4-aminophenyl)-2-[(tert-butoxycarbonyl)amino]propanoate (20.8 g, 54.7 mmol) and N-chlorosuccinimide (8.04 g, 60.2 mmol) were dissolved in N,N-dimethylformamide (339 mL) and allowed to stir overnight. The reaction was diluted with water, extracted with diethyl ether, washed with saturated aqueous sodium chloride then dried over MgSO4, filtered and the solvent evaporated. The mixture was purified by silica gel chromatography, eluting with 30% ethyl acetate in hexanes to give an orange oil (13.7 g, 62%). 1H NMR (400 MHz, CDCl3): δ 7.34 (m, 5H), 6.95 (s, 1H), 6.72 (d, J=7.8 Hz, 1H), 6.61 (d, J=8.0 Hz, 2H), 5.18 (d, J=12.1 Hz, 1H), 5.10 (d, J=12.3 Hz, 1H), 4.98 (d, J=8.2 Hz, 1H), 4.71 (d, J=5.3 Hz, 1H), 4.54 (m, 1H), 3.97 (m, 2H), 2.96 (m, 2H), 1.43 (s, 9H); LCMS found for C21H25ClN2NaO4 (M+Na)+: m/z=427.0.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialthen dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe mixture was purified by silica gel chromatography
  7. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8eab7bb77e104c2e900aa8ea7bc5eae5
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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