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Diisopropylethylamine → {1-[Allyl-(2,4-dimethoxy-benzyl)-carbamoyl]-2,2-dimethyl-but-3-enyl}-carbamic acid tert-butyl ester

HRID 852012
Notes
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Reaction equation

HRID 852012 reaction equation
[CH3:1][C:2]([CH3:17])([O:4][C:5]([NH:7][CH:8]([C:12]([CH3:16])([CH3:15])[CH:13]=[CH2:14])[C:9]([OH:11])=O)=[O:6])[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:49]([NH:52][CH2:53][C:54]1[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][C:55]=1[O:62][CH3:63])[CH:50]=[CH2:51]>CN(C)C=O>[C:2]([O:4][C:5](=[O:6])[NH:7][CH:8]([C:9](=[O:11])[N:52]([CH2:49][CH:50]=[CH2:51])[CH2:53][C:54]1[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][C:55]=1[O:62][CH3:63])[C:12]([CH3:16])([CH3:15])[CH:13]=[CH2:14])([CH3:1])([CH3:3])[CH3:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4722371N-(2,4-Dimethoxybenzyl)prop-2-EN-1-amineHCID 11099301O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 113685192-((Tert-butoxycarbonyl)amino)-3,3-dimethylpent-4-enoic acid

Product 1

HCID 69507319{1-[Allyl-(2,4-dimethoxy-benzyl)-carbamoyl]-2,2-dimethyl-but-3-enyl}-carbamic acid tert-butyl ester
Yield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-[[(1,1-Dimethylethoxy)carbonyl]amino]-3,3-dimethyl-4-pentenoic acid (322 mg, 1.32 mmol; Synthesis see Bartlett, Paul A.; Barstow, James F. Journal of Organic Chemistry (1982), 47(20), 3933-41) was dissolved in dimethylformamide (6 ml) and activated with the coupling reagent TATU (469 mg, 1.46 mmol) and Hünig's base (376 mg, 2.91 mmol) for 2 min. Allyl-(2,4-dimethoxy-benzyl)-amine (274 mg, 1.32 mmol) dissolved in dimethylformamide (2 ml) was added and the mixture was stirred overnight. The solvent was evaporated and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, 1 M KHSO4 solution and brine. After drying with magnesiumsulfate the organic layer was concentrated and purified by flash chromatography (heptane/ethyl acetate=2:1) to yield 510 mg (89%) of {1-[allyl-(2,4-dimethoxy-benzyl)-carbamoyl]-2,2-dimethyl-but-3-enyl}-carbamic acid tert-butyl ester; MS: m/e=433.6 (MH+), 450.6 (M+NH4+).

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 solution, 1 M KHSO4 solution and brine
  5. dry with materialAfter drying with magnesiumsulfate the organic layer
  6. concentrationwas concentrated
  7. custompurified by flash chromatography (heptane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-20f5b689af694b6480039814d9eb0698
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253158B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes