P-Toluic Acid → HCID 11960231, compound

HRID 643055Notes

Reaction equation

HRID 643055 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=O)=[CH:35][CH:34]=1.[NH2:42][C@H:43]1[CH2:48][CH2:47][CH2:46][C@:45]([C:50]#[C:51][C:52]2[CH:57]=[CH:56][CH:55]=[C:54]([Cl:58])[CH:53]=2)([OH:49])[CH2:44]1>CC(N(C)C)=O>[Cl:58][C:54]1[CH:53]=[C:52]([C:51]#[C:50][C@:45]2([OH:49])[CH2:46][CH2:47][CH2:48][C@H:43]([NH:42][C:37](=[O:39])[C:36]3[CH:35]=[CH:34][C:33]([CH3:32])=[CH:41][CH:40]=3)[CH2:44]2)[CH:57]=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 7470P-Toluic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67204565HCID 67204565, compound

Product 1

HCID 11960231HCID 11960231, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A solution of TBTU (2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate)(29.9 mg, 0.093 mmol) in DMA (0.23 ml) and DIPEA (36 μl, 0.213 mmol) was added to solid 4-methylbenzoic acid (11.6 mg, 0.085 mmol) under argon atmosphere at room temperature. After stirring for 20 min., a solution of (1S,3S)-3-amino-1-(3-chloro-phenylethynyl)-cyclohexanol (21.2 mg, 0.085 mmol) in DMA (0.43 ml) was added and the crude reaction mixture was purified without further treatment after stirring for 24 h on a preparative LC/MS system, yielding the title compound (25.1 mg, 0.068 mmol).

Workup

  1. customthe crude reaction mixture
  2. customwas purified without further treatment
  3. stirringafter stirring for 24 h on a preparative LC/MS system

Sources & evidence

ORD record
ord-1d21411b6e94493dba8dfabf4c996d07
Source dataset
uspto-grants-2010_04
Patent number
US07696379B2

Reaction notes

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