1,2-Dichloroethane → 2-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methoxy-methyl-amide

HRID 424110Notes

Reaction equation

HRID 424110 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:26]([CH:37]([CH3:39])[CH3:38])=[CH:25][C:10]=1[C:11]([N:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:22]([OH:24])=O)[CH:19]=2)[CH2:14]1)=[O:12])C1C=CC=CC=1.C(Cl)CCl.[CH:44]1[CH:45]=[CH:46][C:47]2N(O)N=N[C:48]=2[CH:49]=1.CCN(CC)CC.Cl.[CH3:62][NH:63][O:64][CH3:65]>CN(C=O)C>[CH3:65][O:64][N:63]([CH3:62])[C:22]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([C:11](=[O:12])[C:10]1[CH:25]=[C:26]([CH:37]([CH3:39])[CH3:38])[C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:28][C:9]=1[O:8][CH2:1][C:49]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[CH2:21]2)=[O:24]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 590070032-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

Product 1

HCID 469151852-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methoxy-methyl-amideYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid (Preparation D6) (1.76 g, 3.39 mmol), EDC (0.78 g, 4.06 mmol), HOBT (0.55 g, 4.06 mmol), Et3N (1 ml, 6.78 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.36 g, 3.72 mmol) in DMF (20 ml) was stirred at room temperature for 48 hours, then evaporated under vacuum. The crude material was dissolved in ethyl acetate and extracted twice with saturated NaHCO3, organics washed with brine, dried (MgSO4), filtered then evaporated to give 1.84 g of 2-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methoxy-methyl-amide. MS: [M+H]+ 563.

Workup

  1. customevaporated under vacuum
  2. dissolutionThe crude material was dissolved in ethyl acetate
  3. extractionextracted twice with saturated NaHCO3
  4. washorganics washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthen evaporated

Sources & evidence

ORD record
ord-3d1296ff2e2a4a0ebd519027f179174d
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Reaction notes

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