1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 87834573, compound

HRID 404924Notes

Reaction equation

HRID 404924 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[S:9][C:8]([O:10][C:11]2[CH:12]=[N:13][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:15][CH:16]=2)=[N:7][CH:6]=1)[NH2:4].[C:21]([NH:28][C@H:29]([C:31](O)=[O:32])[CH3:30])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(N=C=NCCCN(C)C)C>ClCCl>[NH2:4]/[C:3](=[N:2]\[O:1][C:31](=[O:32])[CH:29]([NH:28][C:21](=[O:22])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH3:30])/[C:5]1[S:9][C:8]([O:10][C:11]2[CH:12]=[N:13][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:15][CH:16]=2)=[N:7][CH:6]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 91514082HCID 91514082, compound

Product 1

HCID 87834573HCID 87834573, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of Example 81B (370 mg, 1.25 mmol) and N-Boc-alanine (286 mg, 1.51 mmol) in dichloromethane (10 mL) was treated with 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide (361 mg, 1.88 mmol). The reaction was stirred for 15 minutes at 25° C. Dichloromethane (50 mL) was added and the resulting mixture was washed with saturated sodium carbonate (50 mL) and brine (50 mL). The organic layers were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes to provide 482 ng of the title compound (83%) as white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.26-1.35 (m, J=5.70, 5.70 Hz, 9H) 1.39 (s, 9H) 4.12-426 (m, 1H) 5.14-5.31 (m, 1 H) 6.86 (d, J=8.82 Hz, 1H) 7.05 (s, 2H) 7.37 (d, J=7.72 Hz, 1H) 7.83 (dd, J=9.19, 2.94 Hz, 1H) 7.87 (s, 1H) 8.26 (d, J=2.94 Hz, 1H); MS (ESI) m/z 466.0 (M+H)+.

Workup

  1. washthe resulting mixture was washed with saturated sodium carbonate (50 mL) and brine (50 mL)
  2. dry with materialThe organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e3e37a8c074d453190a437d1fd475a06
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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