Triethylamine → N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-(2-oxopyrrolidin-1-yl)-5-phenoxybenzamide

HRID 1612484Notes

Reaction equation

HRID 1612484 reaction equation
[CH2:1]([C@H:8]([NH:23][C:24](=[O:38])[C:25]1[CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[CH:28]=[C:27]([OH:37])[CH:26]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:39]1(B(O)O)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([C@H:8]([NH:23][C:24](=[O:38])[C:25]1[CH:26]=[C:27]([O:37][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:28]=[C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[CH:30]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 10218066N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-hydroxy-5-(2-oxopyrrolidin-1-yl)-benzamide

Product 1

HCID 10312269N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-(2-oxopyrrolidin-1-yl)-5-phenoxybenzamideYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-[(1S,2S,4R)-1-benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzamide (E2) (52 mg, 0.1 mmol), benzeneboronic acid (25 mg, 0.2 mmol), cupric acetate (18 mg, 0.1 mmol) and powdered 4 A molecular sieves in dichloromethane (1 ml) were treated with triethylamine (0.070 ml, 0.5 mmol). After stirring for 40 hrs at room temperature, the mixture was partitioned between ethyl acetate and 2N HCl and the product was extracted into ethyl acetate. The extracts were washed with sodium bicarbonate solution and brine and then dried (Na2SO4) and concentrated. Chromatography on silica gel (elution with ethyl acetate) gave E11 as a white solid (24 mg).

Workup

  1. customthe mixture was partitioned between ethyl acetate and 2N HCl
  2. extractionthe product was extracted into ethyl acetate
  3. washThe extracts were washed with sodium bicarbonate solution and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-78d5ea84a3ab4f7a99f9f62734c8bb09
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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