Di-tert-butyl dicarbonate → HCID 11852483, compound

HRID 2358379Notes

Reaction equation

HRID 2358379 reaction equation
C(C1C=CC(CN)=CC=1)(C)(C)C.O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.[C:28]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][N:39]=[C:40]=[O:41])=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29].[NH2:42][CH2:43][C:44]1[CH:49]=[C:48]([CH:50]=[CH2:51])[C:47]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])=[C:46]([CH3:57])[CH:45]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:28]([C:32]1[CH:33]=[CH:34][C:35]([CH2:38][NH:39][C:40](=[O:41])[NH:42][CH2:43][C:44]2[CH:49]=[C:48]([CH:50]=[CH2:51])[C:47]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])=[C:46]([CH3:57])[CH:45]=2)=[CH:36][CH:37]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 90495Di-tert-butyl dicarbonateHCID 27356554-tert-ButylbenzylamineHCID 220422271-Tert-butyl-4-(isocyanatomethyl)benzeneHCID 68453767HCID 68453767, compound

Product 1

HCID 11852483HCID 11852483, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-tert-Butyl-benzylamine (1.5 eq, 71.91 μl, 0.44 mmol) was added in CH2Cl2 and then BOC2O (1.5 eq, 0.44 mmol, 101.19 μl) and DMAP (0.2 eq, 0.06 mmol, 7.08 mg) were slowly added. After confirming the synthesis of the 1-tert-Butyl-4-isocyanatomethyl-benzene, N-(4-Aminomethyl-2-methyl-6-vinyl-phenyl)-methanesulfonamide (1 eq, 0.29 mmol, 70.5 mg) and TEA (2 eq, 0.58 mmol, 80.84 μl) were added into the reaction mixture. The reaction mixture was stirred for 12 hr. The reaction mixture was purified according to step 9 of example 7 to obtain N-{4-[3-(4-tert-Butyl-benzyl)ureidomethyl]-2-methyl-6-vinylphenyl}methanesulfonamide (29.75 mg, 23.9%).

Workup

  1. additionwere added into the reaction mixture
  2. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-1c4618e98f514161bad89e349c87fd56
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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