Triethylamine → Ethyl acetate hexane

HRID 2415786Notes

Reaction equation

HRID 2415786 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)NC(C(O)=O)=C2.[CH2:14]([O:16][C:17](=[O:31])[CH2:18]N1C2C=C(N)C=CC=2OCCC1)[CH3:15].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C1COCC1>[CH3:15][CH2:14][O:16][C:17]([CH3:18])=[O:31].[CH3:4][CH2:3][CH2:2][CH2:10][CH2:9][CH3:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69755810HCID 69755810, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 122.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloroindole-2-carboxylic acid (73 mg, 0.37 mmol, 1 eq.), (2-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-acetic acid ethyl ester (93 mg, 0.37 mmol, 1 eq.), and BOP (163 mg, 0.37 mmol, 1 eq.) were dissolved in 5 mL of anhydrous THF in a round bottom flask. Triethylamine was added in a single portion (0.103 mL, 74 mmol, 2 eq.) and reaction mixture stirred at room temperature for 5 hours. The reaction mixture was then concentrated and the residue purified by preparative TLC in 50% AcOEt/hexane affording 79 mg (50% yield) of the product an off-white crystalline solid. LC MS: AP+ 428/430, AP− 426/428.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-93fd17bfa30445c5963c1b4cce41435a
Source dataset
uspto-grants-2004_11
Patent number
US06821977B2

Reaction notes

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