Triethylamine → HCID 11669078, compound

HRID 502553Notes

Reaction equation

HRID 502553 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH2:13])=[N:2]1.[C:14]([O:18][C:19]([N:21](C1C=CC=CC=1)[CH2:22][C:23](O)=[O:24])=[O:20])([CH3:17])([CH3:16])[CH3:15].Cl.CN(C)CCCN=C=NCC.ON1[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=2N=N1.C(N(CC)CC)C>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH:13][C:23](=[O:24])[C@@H:22]([NH:21][C:19](=[O:20])[O:18][C:14]([CH3:15])([CH3:16])[CH3:17])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[N:2]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16768374N1-(benzo[d]isothiazol-3-yl)ethane-1,2-diamineHCID 21905636N-(tert-Butoxycarbonyl)-N-phenylglycine

Product 1

HCID 11669078HCID 11669078, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N1-(benzo[d]isothiazol-3-yl)ethane-1,2-diamine (600 mg, 3.1 mmol), N α (t-butoxycarbonyl)phenylglycine (850 mg, 3.4 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (650 mg, 3.4 mmol), 1-hydroxybenzotriazole (520 mg, 3.4 mmol) and triethylamine (950 μL, 6.8 mmol) in dichloromethane (50 mL) was allowed to stir at room temperature overnight. The reaction mixture was washed successively with 1N aqueous hydrochloric acid, saturated sodium bicarbonate solution and water, then dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure. Purification by flash column chromatography, on silica gel, eluting with a mixture of 30% ethyl acetate in hexanes and selected fractions were combined and concentrated under reduced pressure to give (S)-tert-butyl 2-(2-(benzo[d]isothiazol-3-ylamino)ethylamino)-2-oxo-1-phenylethylcarbamate (720 mg) as a white solid. 1H NMR (300 MHz, CDCl3): 7.78 (d, 1H), 7.61 (d, 1H), 7.49 (t, 1H), 7.30 (t, 1H), 7.21 (m, 2H), 7.18 (m, 2H), 6.95 (t, 1H), 5.66 (m, 2H), 5.10 (broad s, 1H), 3.62 (m, 4H), 1.39 ppm (s, 9H). MW=427 confirmed by LC-MS, tr=13.38 min (Method Y) MH+=428.

Workup

  1. washThe reaction mixture was washed successively with 1N aqueous hydrochloric acid, saturated sodium bicarbonate solution and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customPurification by flash column chromatography
  6. washon silica gel, eluting with a mixture of 30% ethyl acetate in hexanes
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0ef1e469fa64f6ea0919fcbee0633b8
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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