1,1'-(Diazomethylene)bis(benzene) → Benzhydryl 2-{4-[2-(acetylamino)-3-(allyloxy)-3-oxopropyl][tert-butoxy(oxo)acetyl]-2-ethylanilino}benzoate

HRID 488639Notes

Reaction equation

HRID 488639 reaction equation
[C:1]([NH:4][CH:5]([C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])[CH2:6][C:7]1[CH:31]=[CH:30][C:10]([N:11]([C:21](=[O:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])=[C:9]([CH2:32][CH3:33])[CH:8]=1)(=[O:3])[CH3:2].[C:40]1([C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[N+]=[N-])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CC(C)=O>[C:1]([NH:4][CH:5]([C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])[CH2:6][C:7]1[CH:31]=[CH:30][C:10]([N:11]([C:21](=[O:29])[C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([O:16][CH:46]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:15])=[C:9]([CH2:32][CH3:33])[CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 222719002-{4-[2-(Acetylamino)-3-(allyloxy)-3-oxopropyl][tert-butoxy(oxo)acetyl]-2-ethylanilino}benzoic acid

Product 1

HCID 22271913Benzhydryl 2-{4-[2-(acetylamino)-3-(allyloxy)-3-oxopropyl][tert-butoxy(oxo)acetyl]-2-ethylanilino}benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 2-{4-[2-(acetylamino)-3-(allyloxy)-3-oxopropyl][tert-butoxy(oxo)acetyl]-2-ethylanilino}benzoic acid in acetone was added diphenyldiazomethane (until all starting material was consumed as evident by monitoring via TLC). The reaction mixture was concentrated under reduced pressure, purified on silica gel using ethyl acetate as eluent to provide the titled compound. MS (ESI(+)) m/e 705 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.51-8.01 (m, 2H), 7.73-6.86 (m, 16H), 5.93-5.78 (m, 1H), 5.34-5.10 (m, 2H), 4.57-4.40 (m, 3H), 3.10-2.84 (m, 2H), 2.58-2.42 (m, 2H), 1.82-1.77 (m, 3H), 1.22-0.78 (m, 3H), 1.07, 1.05, 1.00 (s, s, s, 9H).

Workup

  1. customwas consumed as evident
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified on silica gel

Sources & evidence

ORD record
ord-eca21f5ece0a46539889c98f800b3f68
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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