1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 19362682, compound

HRID 1971127Notes

Reaction equation

HRID 1971127 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([F:16])([CH3:15])[CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN.[CH:20]([N:23](CC)C(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>ClCCl>[F:16][C:13]([CH3:15])([CH3:14])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]([NH:23][CH3:20])=[O:11]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 6364545Methylamine hydrochlorideHCID 46737272DL-Valine, N-[(1,1-diMethylethoxy)carbonyl]-3-fluoro-

Product 1

HCID 19362682HCID 19362682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Intermediate 66A (290 mg, 1.23 mmol) and methylamine hydrochloride (100 mg, 1.48 mmol) were dissolved in dichloromethane (5 mL) and N,N-diisopropylethylamine (0.65 mL, 3.70 mmol). 1-Hydroxybenzotriazole hydrate (283 mg, 1.85 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (354 mg, 1.85 mmol) were added, and the solution was stirred for 18 hours. The mixture was diluted additional dichloromethane and washed with saturated aqueous ammonium chloride solution and brine. The organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure to provide intermediate 66B as an off-white solid in quantitative yield. 1H-NMR (400 MHz, (CD3)2SO) δ: 1.27 (d, 3H), 1.32 (d, 3H), 1.37 (s, 9H), 2.59 (d, 3H), 4.14 (dd, 1H), 6.72 (d, 1H), 7.93 (q, 1H).

Workup

  1. washwashed with saturated aqueous ammonium chloride solution and brine
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79460d0dd2414e5080fa8e0de02d43cc
Source dataset
uspto-grants-2013_04
Patent number
US08431565B2

Reaction notes

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