Triethylamine → HCID 15614966, compound

HRID 620352Notes

Reaction equation

HRID 620352 reaction equation
O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:39][CH3:40])[C:31]=2[C:35]([F:38])([F:37])[F:36])[C:26]=1[C:41](O)=[O:42].Cl.[C:45]([O:49][C:50](=[O:53])[CH2:51][NH2:52])([CH3:48])([CH3:47])[CH3:46].C(N(CC)CC)C>CN(C)C=O.O>[Cl:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:39][CH3:40])[C:31]=2[C:35]([F:37])([F:38])[F:36])[C:26]=1[C:41]([NH:52][CH2:51][C:50]([O:49][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:53])=[O:42]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 15614961HCID 15614961, compound

Product 1

HCID 15614966HCID 15614966, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole hydrate (2.45 g, 1.5 eq) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.78 g, 1.2 eq) was added to a stirred solution of 2-chloro-6-methoxy-5-(trifluoromethyl)naphthoic acid (3.69 g, 12.11 mmol, prepared by the process of Step 3, Example 12) in dry dimethylformamide (78 mL). After stirring 11/2 hours at room temperature, glycine t-butyl ester hydrochloride (4.06 g, 2 eq) and triethylamine (dried over KOH, 5.8 mL, 3.3 eq) were added. After stirring 3 hours the reaction mixture was diluted with water (1 L) and extracted with ether (3×350 mL). Silica gel was added to the extracts and the solvent was removed. The absorbate was flash chromatographed (70:30 petroleum ether:ethyl acetate) to give the title compound as a white solid (3.95 g, 80%), m.p. 166°-167° C.

Workup

  1. stirringAfter stirring 3 hours the reaction mixture
  2. extractionextracted with ether (3×350 mL)
  3. additionSilica gel was added to the extracts
  4. customthe solvent was removed
  5. customchromatographed (70:30 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-9011e5ce67a648e780a8bbf991317495
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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