Diisopropylethylamine → tert-butyl N-[N-[2-(2,4,6-trimethylphenoxy)acetyl]carbamimidoyl]carbamate

HRID 873774Notes

Reaction equation

HRID 873774 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[O:9][CH2:10][C:11]([OH:13])=O.C([N:18](C(C)C)CC)(C)C.N[N:25]([CH:33]=[NH:34])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].O.ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[NH:18]=[C:33]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[NH:34][C:11](=[O:13])[CH2:10][O:9][C:2]1[C:1]([CH3:14])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=1[CH3:8]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 8535732-(2,4,6-Trimethylphenoxy)acetic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 86691067Tert-butyl amino(imino)methylcarbamate

Product 1

HCID 149434105tert-butyl N-[N-[2-(2,4,6-trimethylphenoxy)acetyl]carbamimidoyl]carbamateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mesityloxyacetic acid (89.3 g; 460 mmol), diisopropylethylamine (297.1 g; 2.3 mol), tert-butyl amino(imino)methylcarbamate (76.8 g; 480 mmol), and 1-hydroxybenzotriazole monohydrate (62.4 g; 460 mmol) were dissolved in N,N-dimethylformamide (1.0 L), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (183.1 g; 460 mmol) was added thereto, and the mixture was stirred for 25 hours at room temperature. The precipitated crystals were collected by filtration, washed with ethyl acetate and then dried to give 135.2 g of the title compound (yield 88%).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-650c628ffb51452bbb7f55b577ff821a
Source dataset
uspto-grants-2015_03
Patent number
US08975411B2

Reaction notes

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